Herbicidal sulfonamides

ABSTRACT

Novel compounds of Formula I are useful as herbicides and plant growth regulants.

RELATED APPLICATION

This is a division of application Ser. No. 108,646, filed Oct. 15, 1987,now U.S. Pat. No. 4,786,314, which, in turn, is a continuation-in-partof Ser. No. 041,790, filed Apr. 23, 1987, now abandoned, which is adivision of 860,229, filed May 12, 1986, now U.S. Pat. No. 4,678,498,which, is a continuation-in-part of 743,955, filed June 12, 1985, nowabandoned.

BACKGROUND OF THE INVENTION

EP-A-44,209 discloses herbicidal sulfonamides of formula ##STR1##wherein R is H, F, Cl, Br, NO₂, CF₃, C₁ -C₃ alkyl or C₁ -C₃ alkoxy;

R₁ is H, Cl or C₁ -C₄ alkyl;

R₂ is H or CH₃ ; and

L is, among other values, CO₂ R₁₀, CONR₃ R₄, CN, Cl, Br, NR₃ R₄,S(O)_(n) R₇, SO₂ NR₃ R₄ and OR₉.

EP-A-112,803 discloses, in part, herbicidal sulfonamides of formula##STR2##

South African Patent Application 84/2722 discloses herbicidalsulfonamides of formula ##STR3## wherein A is CR₆ R₇ XR₈, CR₉ R₁₀ R₁₁ orCHR₇ SCQR₂₁ ;

R₉ and R₁₀ are, among other values, H or CH₃ ; and

R₁₁ is COR₂₄ or a C₁ -C₄ alkyl group substituted with, among othervalues, CN, NO₂, OH, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₁ -C₄alkylsulfinyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkoxy, NR₁₂ R₁₃ and SO₂NR₁₅ R₁₆.

EP-A-162,723 discloses 2,5-substituted herbicidal sulfonamides offormula ##STR4## wherein R is H or CH;

R₁ is C₁ -C₃ alkyl; and

R₂ is C₂ -C₆ alkoxy, C₁ -C₆ alkylthio, C₃ -C₆ alkenyl, C₃ -C₆alkynyloxy, C₃ -C₆ alkenylthio, C₃ -C₆ alkynylthio, OCH₂ CH₂ OCH₃, OCH₂CH₂ SCH₃, CH₂ F, CHF₂, OCF₂ H, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, OCH₂ CH₂Cl, C₂ -C₆ alkyl substituted with 1-3 atoms of F or Cl or C₁ -C₄ alkylsubstituted with C₁ -C₂ alkoxy or C₁ -C₂ alkylthio;

U.S. Pat. No. 4,310,346 discloses herbicidal benzensulfonylureascontaining an o-sulfonamide moiety which may contain an optionalfloating substituent selected from F, Cl, Br, C₁ -C₃ alkyl, NO₂, OCH₃,C(O)R_(d), CH₂ OR_(d), CF₃, NH₂, NMe₂, CN, CH₂ S(O)_(n) CH₃, S(O)_(n)CH₃, NHC(O)R_(d) or NHCO₂ R_(d) ; wherein n is 0, 1 or 2 and R_(d) is C₁-C₃ alkyl.

U.S. Pat. No. 4,600,428 disclosesN-(cyclopropylpyrimidinyl)-N-aryl-sulfonylyreas of the formula ##STR5##wherein Ar is a phenyl group ##STR6## or a naphthyl group and Q is agroup X--A or R₃ ;

A is alkynyl, alkyl which is unsubstituted or substituted by halogen,alkoxy, alkylthio, alkylsylfinyl, alkylsulfonyl, haloalkoxy,haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl, or alkenyl whichis unsubstituted or substituted by the substituents given above foralkyl, or A is a phenyl or benzyl group;

E is methine;

X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge;

Z is oxygen or sulfur;

R₁ is hydrogen, alkyl or alkoxy;

R₂ is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino,di-alkylamino, cycloalkyl or alkoxyalkyl, R₃ is hydrogen, halogen,alkyl, alkenyl, haloalkyl, --CO--NR₈ R₉, --CN, --COR₁₀, --NR₁ R₇ or--NR₁ --COR₁₂ ;

R₄ is hydrogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy,halogen, or alkoxyalkyl;

R₅ is independently selected from the same groups as R₃ or --X--R₆ ;

R₆ and R₇ are each alkyl, alkenyl or alkynyl;

R₈ and R₉ independently of one another are each hydrogen, alkyl, alkenylor alkynyl;

R₁₀ is hydrogen, alkyl or haloalkyl;

R₁₁ is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, phenyl or benzyl;and

R₁₂ is the same as R₁ but independent thereof.

South African Patent Application 84/5216 discloses herbicidalsulfonamides of formula ##STR7## in which R₁ and R₂ independently of oneanother denote hydrogen, (C₁ -C₄)-alkyl, (C₁ -C₄)-alkoxy or (C₁-C₄)-alkylthio which are optionally monosubstituted or poly-substitutedby halogen, NO₂, (C₁ -C₄)-alkoxycarbonyl, --(C₁ -C₄)--S(O)_(n) --, (C₁-C₄ -alkyl)--N(R₉ SO₂ --, (C₁ -C₄)-alkenyloxy, (C₁ -C₄)-alkynyloxy,--OSO₂ --(C₁ -C₄)-alkyl, --OSO₂ CF₃, --CONHR₃ or --CON(R₃₂ ;

R₃ and R₄ independently of one another denote hydrogen or (C₁-C₄)-alkyl;

R₅ denotes hydrogen, halogen, (C₁ -C₄)-alkylamino, di(C₁-C₄)-alkylamino, (C₁ -C₄)-alkyl which is optionally mono-substituted orpoly-substituted by halogen, (C₁ -C₃)-alkoxy or (C₁ -C₃)-alkylthio, ordenotes (C₁ -C₄)-alkoxy, (C₁ -C₄)-alkylthio, allyloxy or propargyloxy;

R₆ and R₇ independently of one another denote hydrogen, (C₁ -C₄)-alkyl,(C₁ -C₄)-halogenoalkyl, halogen or (C₁ -C₂)-alkoxy-(C₁ -C₂)-alkyl;

R₈ denotes (C₁ -C₄)-alkyl, (C₂ -C₄)-alkenyl or benzyl;

R₉ denotes (C₁ -C₄)-alkyl which is optionally substituted by CN or (C₁-C₄)-alkoxycarbonyl, or denotes (C₁ -C₄)-alkoxy;

m denotes the number 1 to 3;

n denotes the number 0 to 2; and

X denotes a methine group or nitrogen.

SUMMARY OF THE INVENTION

This application pertains to novel compounds of Formula I,agriculturally suitable compositions containing them and theirmethod-of-use as preemergent and/or postemergent herbicides or plantgrowth regulants. ##STR8## wherein E is CH₂ or a single bond;

W is O or S;

R is H or CH₃ ;

R₁ is F, Cl, Br, NO₂, C₁ -C₄ alkyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl,C₂ -C₄ alkynyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, OCH₂ CH₂ OCH₃, C₁ -C₄haloalkoxy, C₃ -C₄ alkenyloxy, C₂ -C₄ haloalkenyloxy, C₃ -C₄ alkynyloxy,CO₂ R₃, CONR₄ R₅, SO₂ NR₄ R₅, SO₂ N(OCH₃)CH₃, S(O)_(n) R₆, OSO₂ R₇, C₁-C₂ alkyl substituted with C₁ -C₂ alkoxy, OH or C₁ -C₂ alkylthio, CH₂CN, C₆ H₅, ##STR9## R₂ is CH(R₁₆)CN, CH(R₁₇)SCN, ##STR10## R₃ is C₁ -C₄alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, ##STR11## CH₂ CH₂ Cl, CH₂ CH₂ F,or C₁ -C₂ alkyl substituted with OCH₃ or SCH₃ ;

R₄ is C₁ -C₃ alkyl;

R₅ is H or C₁ -C₃ alkyl;

R₄ and R₅ may be taken together to form (CH₂)₃ or (CH₂)₄ ;

R₆ is C₁ -C₃ alkyl, CH₂ CH═CH₂ or CH₂ C.tbd.CH;

R₇ is C₁ -C₃ alkyl or N(CH₃)₂ ;

R₈ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, CH₂ CH₂ Cl, CH₂CH₂ F, C₁ -C₂ alkyl substituted with OCH₃ or SCH₃ or C₃ -C₆ cycloalkyl;

R₉ is C₁ -C₂ alkyl;

R₁₀ and R₁₁ are independently C₁ -C₂ alkyl, C₁ -C₂ alkoxy, C₁ -C₂alkylthio, NHCH₃ or N(CH₃)₂ ;

R₁₂ and R₁₃ are independently H or C₁ -C₂ alkyl;

R₁₄ is C₁ -C₃ alkyl;

R₁₅ is H or CH₃ ;

R₁₆ is H, C₁ -C₂ alkyl or F;

R₁₇ is H or C₁ -C₂ alkyl;

R₁₈ is C₁ -C₂ alkyl;

R₁₉ is H, Si(CH₃)₃ or C₁ -C₂ alkyl;

R₂₀ is H or C₁ -C₂ alkyl;

p is 1 or 2;

n is 0, 1, or 2;

A is ##STR12## X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy,C₁ -C₄ haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, halogen, C₂-C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino or di(C₁-C₃ alkyl)amino;

Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl)amino, C₃ -C₄alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅ alkylthioalkyl, C₂ -C₅alkylsulfinylalkyl, C₂ -C₅ alkylsulfonylalkyl, C₁ -C₄ haloalkyl, C₂ -C₄alkynyl, C₃ -C₅ cycloalkyl, azido, cyano, ##STR13## m is 2 or 3; Q₁ andQ₂ are independently O or S;

R_(a) is H or C₁ -C₃ alkyl;

R_(b) and R_(c) are independently C₁ -C₃ alkyl;

Z is CH, N, CCH₃, CC₂ H₅, CCl or CBr;

Y₁ is O or CH₂ ;

X₁ is CH₃, OCH₃, OC₂ H₅ or OCF₂ H;

X₂ is CH₃, C₂ H₅ or CH₂ CF₃ ;

Y₂ is OCH₃, OC₂ H₅, SCH₃, SC₂ H₅, CH₃ or CH₂ CH₃ ;

X₃ is CH₃ or OCH₃ ;

Y₃ is H or CH₃ ;

X₄ is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl;

Y₄ is CH₃, OCH₃, OC₂ H₅ or Cl;

and their agriculturally suitable salts; provided that

(1) when X is halogen, then Z is CH and Y is OCH₃, OC₂ H₅, NH₂, NHCH₃,N(CH₃)₂, OCF₂ H or N(OCH₃)CH₃ ;

(2) when X or Y is C₁ haloalkoxy, then Z is CH;

(3) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH₃,OCH₃, OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH,OCH₂ CH₂ OCH₃, CH(OCH₃)₂ or ##STR14## (4) when the total number ofcarbon atoms of X and Y is greater than four, then the combined numberof carbons of R₁ and R₂ is less than or equal to six;

(5) when R₂ is C(O)R₁₇, then R₁ is other than C₁ -C₄ haloalkyl or C₂alkyl substituted with C₁ -C₂ alkoxy, OH or C₁ -C₂ alkylthio, and Y isother than cyclopropyl;

(6) when Y is C₂ -C₅ alkylthioalkyl, C₂ -C₅ alkylsulfinylalkyl or C₂ -C₅alkylsulfonylalkyl, then R₂ is other than CH(R₁₇)NO₂ ;

(7) X₄ and Y₄ are not simultaneously Cl; and

(8) when R₂ is C(O)R₁₇ then R₁ is other than SO₂ NR₄ R₅ and SO₂N(OCH₃)CH₃.

In the above definitions, the term "alkyl", used either alone or incompound words such as "alkylthio" or "haloalkyl", denotes straightchain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or thedifferent butyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the differentbutoxy isomers.

Alkenyl denotes straight chain or branched alkenes, e.g., vinyl,1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl,1-propynyl, 2-propynyl and the different butynyl isomers.

Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term "halogen", either alone or in compound words such as"haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as "haloalkyl" said alkyl may bemono-halogenated or fully substituted with halogen atoms, which may bethe same or different. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃and CH₂ CHFCl.

The total number of carbon atoms in a substituent group is indicated bythe C_(i) -C_(j) prefix where i and j are numbers from 1 to 5. Forexample, C₁ -C₃ alkylsulfonyl would designate methylsulfonyl throughpropylsulfonyl, C₂ alkoxyalkoxy would designate OCH₂ OCH₃ ; C₄alkoxyalkoxy would designate the various isomers of an alkoxy groupsubstituted with a second alkoxy group containing a total of 4 carbonatoms, examples including OCH₂ OCH₂ CH₂ CH₃ and OCH₂ CH₂ OCH₂ CH₃ ; as afurther example, C₂ cyanoalkyl would designate CH₂ CN and C₃ cyanoalkylwould designate CH₂ CH₂ CN and CH(CN)CH₃.

Preferred for reasons of increased ease of synthesis and/or greaterherbicidal efficacy are:

1. Compounds of Formula I where

W is O; and

R is H;

2. Compounds of Preferred 1 where

E is a single bond;

X is C₁ -C₂ alkyl, C₁ -C₂ alkoxy, Cl, F, Br, I, OCF₂ H, CH₂ F, CF₃, OCH₂CH₂ F, OCH_(2l) CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; and

Y is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, CH₂ OCH₃, CH₂ OCH₂ CH₃, NHCH₃,N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂OCH₃, CH₂ SCH₃, ##STR15## Z is CH or N; 3. Compounds of Preferred 2where

R₂ is CH₂ CN, CH₂ N₃, ##STR16## 4. Compounds of Preferred 3 where A isA-1. 5. Compounds of Preferred 4 where R₁ is F, Cl, Br, NO₂, C₁ -C₃alkyl, C₁ -C₂ alkyl substituted with 1-3 F or Cl or 1 Br, C₂ -C₃alkenyl, C₂ -C₃ alkenyl substituted with 1-3 F or Cl, C₁ -C₂ alkoxy, C₁-C₂ alkoxy substituted with 1-3 F or Cl or 1-Br, allyloxy, propargyloxy,OC(Cl)═CHCl, CO₂ CH₃, CO₂ C₂ H₅, CO₂ CH₂ CH═CH₂, CO₂ CH₂ CH₂ Cl, CO₂ CH₂CH₂ OCH₃, CONH(C₁ -C₂ alkyl), CONCH₃ (C₁ -C₂ alkyl), SO₂ N(OCH₃)CH₃, SO₂NH(C₁ -C₂ alkyl), SO₂ N(C₁ -C₂ alkyl)₂, S(O)_(n) C₁ -C₃ alkyl, OSO₂ C₁-C₃ alkyl, C₁ -C₂ alkyl substituted with OCH₃ or SCH₃, C₆ H₅ and R₁ --A,R₁ --B, R₁ --C, R₁ --D, R₁ --E, R₁ --F, R₁ --G, R₁ --H, R₁ --I, R₁ --J,R₁ --K, R₁ --L, R₁ --M, R₁ --N, R₁ --O, R₁ --P, R₁ --Q R₁ --R, R₁ --S,R₁ --T, R₁ --U, R₁ --V or R₁ --W;

6. Compounds of Preferred 5 where

X is CH₃, OCH₃, OCH₂ CH₃, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

7. Compounds of Preferred 6 where

R₁ is F, Cl, Br, NO₂, CH₃, CF₃ C₁ -C₂ alkoxy, allyloxy, OC(Cl)═CHCl, CO₂CH₃, CO₂ C₂ H₅, CO₂ NHCH₃, CO₂ N(CH₃)₂, SO₂ NHCH₃ SO₂ N(CH₃)₂, SO₂ CH₃,SO₂ C₂ H₅, OSO₂ CH₃, OSO₂ C₂ H₅, R₁ --A, R₁ --B or R₁ --C.

Specifically preferred for reasons of greatest ease of synthesis and/orgreatest herbicidal efficacy are:

4-(cyanomethyl)-2-[[4,6-dimethoxpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoicacid, methyl ester, m.p. 177°-179° C.; and

4-(cyanomethyl)-2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoicacid, methyl ester, m.p. 160°-163° C.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The compounds of Formula I can be prepared from sulfonamides of FormulaII and heterocyclic amines of Formula III by one or more methodsdescribed in the literature. ##STR17## Several representative routes aredescribed below.

U.S. Pat. No. 4,394,506 (issued 7/19/83) teaches the conversion ofsulfonamides to sulfonyl isocyanates and sulfonyl isothiocyanates, andtheir subsequent coupling with heterocyclic amines of Formula III togive sulfonylureas.

U.S. Pat. No. 4,398,939 (issued 8/16/83) teaches the formation ofn-butylsulfonylureas from sulfonamides followed by phosgenation to givethe sulfonyl isocyanates. Alternatively, the sulfonamides can be treatedwith thionyl chloride followed by phosgenation to afford the sulfonylisocyanates. Additionally, methylcarbamate derivatives of compounds ofFormula III react with sulfonamides in the presence of trimethylaluminumto give sulfonylureas.

U.S. Pat. No. 4,443,245 (issued 4/17/84) teaches two methods for thesynthesis of sulfonylureas. Either a phenyl carbamate of a sulfonamideand a heterocyclic amine, or a sulfonamide and a phenyl carbamate of aheterocyclic amine couple to give a sulfonylurea in an inert solventwith base.

The preparation of sulfonamides from sulfonyl chlorides is widelyreported in the literature; for reviews see: F. Hawking and J. S.Lawrence. "The Sulfonamides, " H. K. Lewis and Co., London, 1950 and E.H. Northey, "The Sulfonamides and Allied Compounds, " ReinholdPublishing Corp., New York, 1948.

Additionally, primary sulfonamides, such as those of Formula II, can beformed by removal of an N-t-butyl protecting group from thecorresponding secondary sulfonamide with trifluoroacetic acid (J. D.Catt and W. L. Matier, J. Org. Chem., 39, 566 (1974)) or polyphosphoricacid (J. G. Lombardino, J. Org. Chem., 36 1971), 1843).

The requisite sulfonyl chlorides may be synthesized by known methods orwith slight modifications thereof, by one skilled in the art. Severalrepresentative teachings are listed below.

Aromatic nitro groups may be transformed into sulfonyl chlorides byreduction, diazotization and coupling with sulfur dioxide/cupricchloride as taught in U.S. Pat. No. 4,310,346 (issued 1/12/82).

European Publication No. 94,821 (published 11/23/83) described thedisplacement of aromatic halides with thiolate anions and subsequentoxidative chlorination to yield sulfonyl chlorides.

Halogen-metal exchange of aromatic halides or proton-metal exchange ofaromatics followed by quenching with sulfur dioxide gives sulfinatesalts. These salts yield sulfonyl chlorides upon reaction withN-chlorosuccinimide as taught in U.S. Pat. No. 4,481,029 (issued11/6/84). Directed proton-metal exchange of aromatic compounds has beenreviewed by Gschwend and Rodriguez, Org. Reactions, 26 (1979), 1.Directed lithiation of aryl-N-t-butylsulfonamides is described by J. G.Lombardino, J. Org. Chem., 36 (1971), 1843. Also, aryllithiums may beconverted directly to arylsulfonyl chlorides with sulfuryl chloride asdescribed in S. N. Bhattacharya, et. al., J. Chem. Soc. C., (1968),1265.

Electrophilic chlorsulfonation of an aromatic ring to give a sulfonylchloride is well known in the literature. This technique works best foralkyl aryl ethers and alkyl aromatics. Its application is described byE. H. Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 511-14and 603-4.

Transformation of phenols to sulfonyl chlorides can be accomplished bythe formation of a thiocarbamate, rearrangement, hydrolysis andoxidative chlorination as described by M. S. Newman and H. A. Kames, J.Org. Chem., 31 (1966), 3980.

Compounds of Formula II can be prepared by a variety of methods known inthe literature. The most universal scheme, where benzyl halides ofFormula IV are reacted with the appropriate reagent, is shown below.##STR18## wherein U is SO₂ NH₂ or a previously described sulfonamideprecursor, and X¹ is Cl, Br or I and R₂ is of the structure --CH(R₁₇)--.Some specific methods are listed below.

NITRILES (R₂ ═CH(R₁₇)CN)

Nitriles can be prepared by nucleophilic displacement of benzyl halides,usually benzyl chlorides or bromides, with potassium or sodium cyanide.Many solvents are applicable, but frequently dimethylsulfoxide is used.Thus, a benzyl bromide of formula IV can be contacted with potassiumcyanide in dimethylsulfoxide for 0.5 h to 24 h at 20° to 140° C. For areview of this reaction, refer to Friedrich and Wallenfels, inRappoport, "The Chemistry of the Cyano Group", pp. 77-86, IntersciencePublishers, New York, 1970.

ISONITRILES (R₂ ═CH(R₁₇)NC)

Heavy metal cyanides and benzylhalides react to give isonitriles. Thereaction is best carried out in the dark using silver cyanide and abenzyl iodide. Typical procedures are given by A. Gautier, Ann. Chem.,142 (1867), 28 and H. L. Jackson and B. C. McKusick, Org. Syn., Col.Vol. IV, 438.

AZIDES (R₂ ═CH(R₁₇)(N₃)

Compounds of Formula II may be prepared by reacting an azide anion witha benzyl halide. Typically sodium azide in alcohol or wet acetone ismixed with a benzyl bromide at 20°-100° C. This nucleophilicdisplacement is reviewed in Biffin, Miller and Paul, in Patai, "TheChemistry of the Azido Group, " pp. 57-119, Interscience Pub., New York,1971.

PHOSPHONATES (R₂ ═CH(R₁₇)P(O)R₁₀ R₁₁)

Alkyl phosphites are heated with benzylic halides to give phosphonates.The reaction is known as the Arbuzov reaction and it is reviewed byArbuzov, Pure Appl. Chem., 9 (1964), 307-335.

AMINES (R₂ ═CH(R₁₇)NR₁₂ R₁₃)

Tertiary amines are prepared by alkylation of a secondary amine with abenzylic halide. The reaction is well documented in the literature.

Primary amines can be prepared by reduction of compounds of Formula IIwhere R₂ is azide. Generally lithium aluminum hydride or hydrogen andpalladium catalyst are used.

NITRO (R₂ ═CH(R₁₇)NO₂)

Nitrites react with benzylic halides to give benzylic nitro compounds.The reaction is usually carried out with sodium nitrite on a benzylicbromide in dimethylformamide or dimethylsulfoxide. When silver nitriteis used, diethyl ether at 0°-25° C. are the preferred reactionconditions. The reaction is exhaustively discussed by N. Kornblum, Org.Reactions, 12 (1962), 101.

SELENO ETHERS (R₂ ═CH(R₁₇)SeR₁₄)

Alkali alkylselenides can be prepared by in situ combination of analkali metal t-butoxide with the selenol HSeR₁₄ in the solvent to beused for the displacement reaction. The selenols, HSeR₁₄, can beprepared by a variety of methods reviewed by D. L. Klayman, "Selenolsand their Derivatives" in Organic Selenium Compounds: Their Chemistryand Biology, D. L. Klayman, W. H. H. Gunther ed., New York, 1973, and K.J. Irgolic and M. V. Kudchadker, "Organic Chemistry of Selenium" inSelenium, R. A. Zingaro, W. C. Cooper ed., Van Nostrand Reinhold, NewYork, 1974.

Benzyl halides may be formed through a variety of methods described inthe literature. Several are listed below.

BENZYLIC CHLORIDES (X¹ ═Cl)

Treatment of alkyl benzene derivatives with N-chlorosuccinimide, NCS, ina suitable solvent, such as carbon tetrachloride or dichloromethane, andcatalyzed by light or a free radical initiator, such asazoisobutyronitrile or benzoyl peroxide, gives the benzylic chloride.

Treatment of a benzylic alcohol with thionyl chloride, either neat or inthe presence of a base such as pyridine, gives the benzylic chloride.For typical examples, see H. Gilman and J. E. Kirby, J. Am. Chem., Soc.,51, 3475 (1929) and M. S. Newman, J. Am. Chem. Soc., 62, 2295 (1940).

BENZYLIC BROMIDES (X¹ ═Br)

Treatment of alkyl benzene derivatives with N-bromosuccinimide by amethod analogous to the case of N-chlorosuccinimide gives the benzylicbromide. Benzylic alcohols in an inert solvent such as benzene ordichloromethane react with phosphorus tribromide to give benzylicbromides.

BENZYLIC IODIDES (X¹ ═I)

Treatment of a benzylic chloride or benzylic bromide with sodium iodidegives the benzylic iodide. The reaction, known as the Finkelsteinreaction, works well in refluxing acetone.

Benzylic alcohols may be treated with iodine and phosphorus (red) orphosphorus (red) and phosphorus (yellow) to give the benzylic iodide.

Compounds of Formua II, where R₂ contains an oxygen functionality, suchas an aldehyde or ketone, may be prepared by a variety of methods knownto one skilled in the art. Two such routes are shown below. ##STR19##

Primary and secondary benzylic halides may be oxidized to aldehydes andketones, respectively using dimethylsulfoxide. For reviews of thisreaction see Durst, Adv. Org. Chem., 285-388 (1969) pp. 343-356 and W.Epstein and F. Sweat, Chem. Rev., 67 (1967), 247-60.

Primary benzylic alochols may be oxidized to aldehydes and secondarybenzylic alcohols may be oxidized to ketones by one skilled in the art.One or more of a variety of methods, such as an oxidizing agent,catalytic dehydrogenation, Oppenauer oxidation or halosuccinimideoxidation may be used.

Acetals, thioacetals, ketals and thioketals are easily prepared by oneskilled in the art from compounds of Formula V.

Oximes, and oxime ethers of Formula Va are easily prepared by oneskilled in the art from compounds of Formula V and hydroxylamine oro-alkyl-hydroxylamine with or without an appropriate base. ##STR20##

Benzylic alcohols and alkyl benzene derivatives are either known or maybe prepared by one skilled in the art.

The heterocyclic amines A-1 to A-7 are either known, disclosed in thisapplication or can be prepared by methods obvious to one skilled in theart.

For a review of the synthesis and reactions of 2-aminopyrimidines (A-1,Z═CH) see The Chemistry of Heterocyclic Compounds, Vol 16,Wiley-Interscience, New York (1962). For a review of the synthesis andreactions of 2-amino-1,3,5-triazines (A-1, Z═N) see The Chemistry ofHeterocyclic Compounds, Vol. 13, Wiley-Interscience, New York (1959), F.C. Schaefer, U.S. Pat. No. 3,154,537 and F. C. Schaefer and K. R.Huffman, J. Org. Chem., 28 (1963), 1812.

The synthesis of bicyclic amines A-2 and A-3 is taught in U.S. Pat. No.4,339,267.

The synthesis of amino furo [2,3-d]pyrimidines, A-4, is taught in U.S.Pat. No. 4,487,626.

The synthesis of aminotriazoles, A-5, is taught in U.S. Pat. No.4,421,550.

The synthesis of aminomethylheterocycles, A-6, is taught in U.S. Pat.No. 4,496,392.

The synthesis of aminocyano heterocycles, A-7, is taught in EuropeanPublication No. 125,864 (published 11/21/84).

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by contacting copounds of Formula Iwith a solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g. hydroxide, alkoxide, carbonate orhydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation for another. Cationic exchange can be effected by directcontacting of an aqueous solution of a salt of a compound of Formula I(e.g., alkali metal or quaternary amine salt) with a solution containingthe cation to be exchanged. This method is most effective when thedesired salt containing the exchanged cation is insoluble in water,e.g., a copper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged. In this method, the cation of the resin isexchanged for that of the original salt of the resin is exchanged forthat of the original salt and the desired product is eluted from thecolumn. This method is particularly useful when the desired salt iswater-soluble, e.g., a potassium, sodium or calcium salt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is furtherillustrated by the following examples.

EXAMPLE 15-Bromomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide

A mixture of 27 g ofN-(1,1-dimethylethyl)-2-methoxy-5-methylbenzenesulfonamide (E. H.Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 603), 19.6 gNBS and 0.3 g azobisisobutyronitrile in 200 ml CH₂ Cl₂ was refluxed andilluminated with a sun lamp. After 8 hours the lamp was turned off andthe reaction was refluxed for another 24 hr. The reaction was allowed tocool. The reaction mixture was washed with 200 ml of a 1:1:1:1 mixtureof brine:sodium sulfite-sodium bicarbonate-water. The organic layer wasdried (MgSO₄), treated with charcoal and filtered through a 5 g plug ofsilica gel. The plug was washed with 100 ml of chloroform. The combinedorganic fractions were evaporated to give 34 g of solid, m.p. 137°-142°C.;

NMR (CDCl₃, 200 MHz)δ: 1.15 (s, CH₃, 9H), 4.0 (s, OCH₃, 3H), 4.45 (s,CH₂, 2H), 4.95 (bs, NH, 1H), 7.0-8.6 (m, ArH, 3H).

EXAMPLE 25-Cyanomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide

A mixture of 1.63 g potassium cyanide and 8 g of the compound fromExample 1 in 50 ml of DMSO was stirred at room temperature overnight.The solution became darker in color with time, going from orange topurple to black. After being stirred overnight the reaction mixture waspartitioned between ethyl acetate and water. The organic layer waswashed with brine, dried (MgSO₄), filtered and the solvent evaporated.The residual red oil was eluted through a dry silica column with 20%ethyl acetate-80% dichloromethane. The product band was isolated to give3.0 g solid m.p. 146°-147° C.;

NMR (CDCl₃, 90 MHz): 1.1 (s, CH₃, 9H), 3.7 (s, CH₂ CN, 2H), 4.0 (s,OCH₃, 3H), 5.0 (s, NH, 1H), 6.9-8.0 (m, ArH, 3H).

EXAMPLE 3 5-Cyanomethyl-2-methoxybenzenesulfonamide

A suspension of 3.0 g of the compound from Example 2 and 0.1 gp-toluenesulfonic acid in 100 ml of dry toluene was refluxed in a flaskequipped with a Dean-Stark apparatus. After being refluxed overnight thesolution was concentrated and allowed to cool. The precipitate wasfiltered off to give 0.5 g light brown solid. The mother liquor waschromatographed over silica gel with 20:73:2:5, ethyl acetate:methylenechloride:methanol:THF to give additional product, m.p. 173°-177° C.;

NMR (DMSO-d₆, 90 MHz)δ: 3.9 (s, OCH₃, 3H), 4.0 (s, CH₂ CN, 2H), 7.1 (bs,NH₂, 2H), 7.2-7.8 (m, ArH, 3H).

EXAMPLE 45-(Cyanomethyl)-N-((4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl)-2-methoxybenzenesulfonamide

To a suspension of 0.3 g of the compound from Example 3 and 0.37 g4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 15 ml of dryacetonitrile was added 0.198 ml DBU. After being stirred overnight theclear solution was diluted with 50 ml of water, acidified with 1N HCland the precipitate was filtered off. The residue was washed with waterand triturated with ether to give 0.44 g solid, m.p. 168°-171° C.(dec.);

IR (nujol) 1711 cm⁻¹ ;

NMR (200 MHz, DMSO-d₆)δ: 3.76 (s, OCH₃, 3H), 3.91 (s, OCH₃, 6H), 4.10(s, CH₂, 2H) 6.02 (s, Het-H, 1H), 7.2-7.9 (m, ArH, 3H), 10.5+12.8 (S,NH, 2X1H).

EXAMPLE 5 5-(Bromomethyl)-2-carboxymethylbenzenesulfonamide

A solution of 3.5 g (0.0153 mole) of5-methyl-2-carboxymethylbenzenesulfonamide, 2.86 g N-bromosuccinimide,0.05 g azobisisobutyronitrile in 50 ml of carbon tetrachloride and 50 mldichloromethane was prepared under a nitrogen atmosphere. The solutionwas refluxed and irradiated with a sun lamp for 4 h. Then 0.6 gN-bromosuccinimide was added. After three hours of further irradiationthe reaction was cooled and filtered to give 4.7 g of a white solid. Thesolid was washed with 200 ml of dichloromethane to leave 1.0 g ofproduct. The mother liquor was eluted through a dry silica gel columnwith 5% diethyl ether/95% dichloromethane to give an additional 2.3 g ofproduct, m.p. 171°-173° C.;

NMR (CDCl₃, 200 MHz)δ: 4.0 (s, OCH₃, 3H), 4.52 (s, CH₂ Br, 2H) 5.76 (s,NH₂, 2H), 7.6-8.2 (m, ArH, 3H).

EXAMPLE 6 5-(Cyanomethyl)-2-carboxymethylbenzenesulfonamide

To a solution of 0.31 g potassium cyanide in 20 ml of drydimethylsulfoxide was added 1.4 g (4.55 mmol) of the compound fromExample 5. After being stirred for 6 h, the reaction mixture waspartitioned between ethyl acetate amd water. The water layer wasneutralized to pH 7, the layers separated and the organic layer wasdried (MgSO₄). This solution was placed on a dry silica gel column andeluted with 40% ethyl acetate/60% hexane followed by 60% ethylacetate/40% hexane. The product band (R_(f) 0.5, 60% ethyl acetate/40%hexane) was extracted with ethyl acetate, concentrated and the residuetriturated with diethyl ether to give 0.26 g of a solid, m.p. 125°-129°C.;

MS (m/e) 254 (M⁺);

IR (Nujol) 1711 cm⁻¹ ;

NMR (200 Mhz, DMSO-d₆)δ: 3.82 (s, OCH₃), 4.24 (s, CH₂ CN), 7.36 (s,NH₂), 7.65 (dd, ArH, 2H), 7.95 (s, ArH, 1H).

EXAMPLE 74-(Cyanomeethyl)-2-[((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)aminosulfonyl]benzoicacid, methyl ester

To a suspension of 0.12 g of the compound from Example 6 and 0.143 g of4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 15 ml of dryacetonitrile was added 72.7 μof 1.8-diazabicyclo[5.4.0]undec-7-ene(DBU). After being stirred at room temperature for one hour, thereaction mixture was diluted with 50 ml of water, acidified with 1Nhydrochloric acid to pH 2 and extracted with ethyl acetate. The organicsolution was dried (MgSO₄), filtered and concentrated to an oil.Trituration of the residue with 3:1 (ethyl ether:acetonitrile) gave 0.16g of a white solid, m.p. 177°-179° C.;

IR (nujol) 1725 cm⁻¹ ;

NMR (DMSO-d₆, 200 MHz)δ: 3.78 (s, OCH₃, 3H), 3.92 (s, OCH₃, 6H), 4.31(s, CH₂, 2H), 6.01 (S, Het-H, 1H), 7.7-8.2 (m, ArH, 3H), 10.6 and 12.7(two s, NH, 2X1H).

EXAMPLE 8 5-Acetyl-2-ethoxybenzenesulfonamide

To a solution of 30.6 g of 4-ethoxyacetophenone in 100 ml of chloroformwas added 40 ml of chlorosulfonic acid dropwise. The reaction was thenrefluxed for five hours after which it was poured into 800 ml of icewater. The reaction mixture was extracted with 400 ml of chloroform. Theorganic layer was washed with brine, dried (MgSO₄) and filtered throughcharcoal. The filtrate was concentrated under reduced essure to give12.3 g of an oil. The oil was dissolved in 200 ml tetrahydrofuran. Thesolution was cooled to 5° C. followed by dropwise addition of 10 ml ofconcentrated ammonium hydroxide. After stirring overnight at roomtemperature, the reaction was partitioned between water and ethylacetate. The organic layer was washed with 1N hydrochloric acid, brine,dried (MgSO₄), filtered and stripped. The residue was crystallized fromacetonitrile/diethyl ether. The solid was washed with methanol and driedto give 2.3 g of solid, m.p. 148°-151° C.;

NMR (90 MHz, CDCl₃)δ: 1.5 (m, CH₃, 3H), 2.55 (s, CH₃, 3H), 4.35 (q, CH₂O, 2H), 5.1 (bs, NH₂), 7.0-8.6 (m, ArH, 3H).

EXAMPLE 95-Acetyl-N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-2-ethoxybenzenesulfonamide

To a stirred suspension of 0.2 g of the compound from Example 8, 0.23 gof 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 10 ml ofdry acetonitrile was added 127 μl of DBU. After being stirred for 1 hr.the mixture was treated with 40 ml of water and 1N HCl in a dropwisemanner until the pH was 3. The precipitate was filtered off and washedwith water and ether/hexane (1/1), to give 0.27 g of a solid, m.p.192°-193° C.;

IR (nujol) 1680 and 1705 cm⁻¹ ;

NMR (200 MHz, DMSO-d₆)δ: 1.1 (t, CH₃, 3H), 2.58 (s, CH₃, 3H) 3.91 (s,OCH₃, 6H), 4.27 (q, CH₂, 2H), 6.03 (s, Het-H, 1H), 7.2-8.4 (m, ArH, 3H),10.6 and 12.7 (s, NH, 2×1H).

The invention is further exemplified, but not limited to the compoundsin Tables I-VII. The compounds depicted in these tables may be preparedby methods described in Examples 1-9, or by modifications thereofapparent to those skilled in the art. ##STR21##

                                      TABLE I                                     __________________________________________________________________________    General Formula I                                                                                                                       m.p.                R.sub.1      R.sub.2      W R  X           Y           Z  (°C.)        __________________________________________________________________________    F            CH.sub.2 CN  O H  OCH.sub.3   H           CH                     F            CH.sub.2 CN  O CH.sub.3                                                                         OCH.sub.3   CH.sub.3    CH                     F            CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   N                      F            CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     F            CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 CH.sub.3                                                                         CH                     F            CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   N                      F            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.2 OCH.sub.3                                                                        CH                     F            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     F            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.2 CH.sub.3                                                                        CH.sub.3    CH                     F            CH.sub.2 P(O)(CH.sub.3).sub.2                                                              O H  OCH.sub.3   CH.sub.3    N                      Cl           CH.sub.2 CN  O H  OCH.sub.3   CH.sub.2 CH.sub.2 OCH(CH.sub.3)                                               .sub.2      CH                     Cl           CH.sub.2 CN  O H  Cl          OCH.sub. 3  CH                     Cl           CH.sub.2 CN  O H  OCH.sub.3   CH(CH.sub.3)(CH.sub.2 OCH.sub.3                                               )           CH                     Cl           CH.sub.2 SCN O H  CH          CH.sub.3    CH.sub.3                                                                         143-153             Cl           CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    N  100-106             Cl           CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH 174-180             Cl           CH.sub.2 SCN O H  Cl          OCH.sub.3   CH oil                 Cl           CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N  oil                 Cl           CH.sub.2 SCN O H  OCH.sub.3   (CH.sub.2).sub.4 CH.sub.2                                                     OCH.sub.2 CH.sub.3                                                                        CH                     Cl           CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    N                      Cl           CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCF.sub.2 H CH.sub.3    CH                     Cl           CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   NH.sub.2    CH                     Cl           CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                    O H  OCH.sub.3   NHCH.sub.3  N                      Br           CH.sub.2 CN  O H  CH.sub.3    NHCH.sub.2 CH.sub.3                                                                       CH                     Br           CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     Br           CH.sub.2 CN  S H  OCH.sub.3   CH.sub.3    N                      Br           CH.sub.2 SCN O H  CH.sub. 2 F OCH.sub.3   CH                     Br           CH.sub.2 SCN O H  OCH.sub.3   NHCH(CH.sub.3).sub.2                                                                      CH                     Br           CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    N                      Br           CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.2 CH.sub.2 F                                                                      OCH.sub.3   CH                     Br           CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   N(CH.sub.3).sub.2                                                                         CH                     Br           CH.sub.2 P(O)(SCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      NO.sub.2     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     NO.sub.2     CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     NO.sub.2     CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     NO.sub.2     CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 CH.sub.2 CH.sub.2                                                    CH.sub.3    N                      NO.sub.2     CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     NO.sub.2     CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.2 CH.sub.2 CH.sub.2                                                               CH                     NO.sub.2     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      NO.sub.2     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       OCH.sub.3   CH                     NO.sub.2     CH.sub. 2 P(O)(OCH.sub.3).sub.2                                                            O H  OCH.sub.3   SCH.sub.2 CH.sub.2 F                                                                      CH                     NO.sub.2     CH.sub.2 P(S)(SCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      CH.sub.3     CH.sub.2 CN  O H  CH.sub.3    SCH.sub.3   CH                     CH.sub.3     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.3     CH.sub.2 SCN O H  OCH.sub.3   SCH(CH.sub.3).sub.2                                                                       N                      CH.sub.3     CH.sub.2 SCN O H  OCH.sub.2 CH(CH.sub.3).sub.2                                                              OCH.sub.3   CH                     CH.sub.3     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  Br          OCH.sub.3   CH                     CH.sub.3     CH.sub.2 P(O)(N(CH.sub.3).sub.2).sub.2                                                     O H  OCH.sub.3   OCH.sub.3   N                      CH.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                          CH.sub.3    OCH.sub.3   CH                     CH.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.2 CH.sub.2 OCH.sub.3                                                              CH                      -n-C.sub.4 H.sub.9                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      CHCH.sub.2   CH.sub.2 CN  O H  F           OCH.sub.3   CH                     CHCHCH.sub.3 CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   N                      CClCCl.sub.2 CH.sub.2 SCN O H  OCH.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2                                                    OCH.sub.3   CH                     CCCH.sub.3   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     CH.sub.2 CCH CH.sub.2 CN  O H  OCH.sub.3   CH.sub.2 CH.sub.3                                                                         N                      CH.sub.2 Cl  CH.sub.2 CN  O H  N(CH.sub.2 CH.sub.3).sub.2                                                                OCH.sub.3   CH                     CH.sub.2 Cl  CH.sub.2 SCN O H  Cl          OCH.sub.3   CH                     CH.sub.2 Br  CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      CH.sub.2 Br  CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     CF.sub.3     CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N                      CF.sub.3     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     CF.sub.3     CH.sub.2 SCN O H  Br          OCH.sub.3   CH                     CF.sub.3     CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 CH.sub.2                                                                         N                      CF.sub.3     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     CF.sub.3     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.2 CH.sub.3                                                                        CH.sub.3    CH                     CF.sub.3     CH.sub.2 NH.sub.2                                                                          O H  OCH.sub.3   H           CH                     CH.sub.2 CHClCH.sub.2 Cl                                                                   CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   N                      CH.sub.2 CF.sub.3                                                                          CH.sub.2 CN  O H  I           OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 CN  O H  OCH.sub.3   CH.sub.2 OCH.sub.3                                                                        CH                     OCH.sub.3    CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   N  166-170°     OCH.sub.3    CH.sub.2 CN  O H  OCH.sub.3   NHCH.sub.3  CH                     OCH.sub.3    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.3    CH.sub.2 CN  O H  OCH.sub.2 CF.sub.2 H                                                                      OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH 168-171°     OCH.sub.3    CH.sub.2 CN  O H  CH.sub.3    CH.sub.3    N                      OCH.sub.3    CH.sub.2 SCN O H  CH.sub.2 Br OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 SCN O H  OCH.sub.3   N(CH.sub.3).sub.2                                                                         N                      OCH.sub.3    CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 SCN O H  OCH.sub.3   SCH.sub.3   N                      OCH.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.2 CF.sub.3                                                                        CH.sub.3    CH                     OCH.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CF.sub.3    CH                     OCH.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.2 Cl CH.sub.3    CH                     OCH.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    N                      OCH.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.3    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  Cl          OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.3    CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  CH.sub.3    CH.sub.3    CH                     OCH.sub.3    CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  Cl          OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.3    CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  OCH.sub.3   CH.sub.3    N                      OCH.sub.3    CH.sub.2 SeCH.sub.3                                                                        O H  OCH.sub.3   OCH.sub.3   CH 135-138             OCH.sub.3    CH.sub.2 SeCH.sub.3                                                                        O H  OCH.sub.3   CH.sub.3    CH 101-110             OCH.sub.3    CH.sub.2 SeCH.sub.3                                                                        O H  Cl          OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 SeCH.sub.3                                                                        O H  CH.sub.3    CH.sub.3    CH 101-103             OCH.sub.3    CH.sub.2 SeCH.sub.3                                                                        O H  OCH.sub.3   OCH.sub.3   N  101-105             OCH.sub.3    CH.sub.2 SeCH.sub.3                                                                        O H  OCH.sub.3   CH.sub.3    N  120-127             OCH.sub.3    CH.sub.2 SeCH.sub.3                                                                        O H  OCH.sub.2 CH.sub.3                                                                        NHCH.sub.3  N                      OCH.sub.3    CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   CH 142-144             OCH.sub.3    CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    CH 129-132             OCH.sub.3    CH.sub.2 N.sub.3                                                                           O H  Cl          OCH.sub.3   CH 144- 146            OCH.sub.3    CH.sub.2 N.sub.3                                                                           O H  CH.sub.3    CH.sub.3    CH 137-142             OCH.sub.3    CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   N  137-142             OCH.sub.3    CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    N  96-101              OCH.sub.3    CH.sub.2 NO.sub.2                                                                          O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 NO.sub.2                                                                          O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 NO.sub.2                                                                          O H  Cl          OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 NO.sub.2                                                                          O H  CH.sub.3    CH.sub.3    CH                     OCH.sub.3    CH.sub.2 NO  O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.3    CH.sub.2 NO.sub.2                                                                          O H  OCH.sub.3   CH.sub.3    N                      OCH.sub.3    CH.sub.2 NC  O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3    CH.sub.2 NC  O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   SCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.2 CHCH.sub.2                                                                      N                      OCH.sub.2 CH.sub.3                                                                         CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH.sub.2 NO.sub.2                                                                          O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  OCH.sub.3   CH.sub.3    N                      OCH(CH.sub.3).sub.2                                                                        CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     o-  -n-C.sub. 4 H.sub.9                                                                    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.2 CCH                                                                             N                      OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 SCN O H  CH.sub.3    OCH.sub.2 CH.sub.2 OCH.sub.3                                                              CH                     OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.2 NH(CH.sub.2 CH.sub.2 CH.sub.3)                                                    O H  OCH.sub.3   OCH.sub.3   CH                     OCF.sub.2 H  CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     OCF.sub.2 H  CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   N                      OCF.sub.2 H  CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 SCH.sub.3                                                                        CH                     OCF.sub.2 H  CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    N                      OCF.sub.2 H  CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    CH                     OCF.sub.2 H  CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     OCF.sub.2 H  CH.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                        O H  OCH.sub.3   OCH.sub.3   N                      OCF.sub.2 H  CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  CH.sub.3    CH.sub.3    CH                     OCH.sub.2 CH.sub.2 F                                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.2 F                                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CF.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 SCN O H  OCH.sub.3   CH.sub.2 CH.sub.2 OCH.sub.2                                                   CH.sub.3    N                      OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  I           OCH.sub.3   CH                     OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 SeCH.sub.3                                                                        O H  CH.sub.3    OCH.sub.3   CH                     OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CN  O H  OCH.sub.3   NH.sub.2    CH                     OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CN  O H  CH.sub. 3   NHCH.sub.2 CH.sub.2 CH.sub.3                                                              CH                     OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.2 CCH                                                                             CH                     OCH.sub.2 CHCH.sub.2                                                                       CH.sub.2 SeCH.sub.2 CH.sub.3                                                               O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CCH                                                                              CH.sub.2 CN  O H  CH.sub.2 C.sub.3                                                                          OCH.sub.3   CH                     OCH.sub.2 CCH                                                                              CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.2 CH.sub.2 CH.sub.2CH.s                                               ub.3        CH                     OCH.sub.2 CCH                                                                              CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CCH                                                                              CH.sub.2 SCN O H  CH.sub.3    CH.sub.2 SCH.sub.                                                                         CH                     OCH.sub.2 CCH                                                                              CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CCH                                                                              CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   N                      OCH.sub.2 CCH                                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.2 SCH.sub.2 CH.sub.2                                                   CH.sub.2    CH                     OCH.sub.2 CCH                                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     OC(Cl)CHCl   CH.sub.2 CN  O H  OCH.sub.3   CH.sub.2 CH.sub.2 F                                                                       N                      OC(Cl)CHCl   CH.sub.2 CN  O H  I           OCH.sub.3   CH                     OC(Cl)CHCl   CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.2 CCH                                                                             CH                     OC(Cl)CHCl   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CCH         N                      OC(Cl)CHCl   CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH 177-179             CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH 172-175             CO.sub.2 CH  CH.sub.2 CN  O H  CH.sub.3    CH.sub.3    CH 174-177             CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N  160-163             CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  CH.sub.2 CH.sub.2                                                                         OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  Cl          OCH.sub.3   CH 181-185             CO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N  126-132             CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  Cl          OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  CH.sub.3    CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH 126                 CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub. 3  CH.sub.3    N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  NHCH.sub.3  OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   CH(OCH.sub.3).sub.2                                                                       CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N  oil                 CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH oil                 CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    CH.sub.3    CH oil                 CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    N  oil                 CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  cyclo-      OCH.sub.3   CH                                                    propyl                                         CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH oil                 CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.2 CF.sub.3                                                                        N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(S)(SCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(SCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH.sub.2                                                                          O H  cyclo-      OCH.sub.3   CH                                                    propyl                                         CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH.sub.2                                                                          O H  Cl          OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH.sub.2                                                                          O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH.sub.2                                                                          O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  CH.sub.3    OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3).sub.2                                                                 O H  Cl          OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                    O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NH(CH(CH.sub.3).sub.2)                                                            O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                        O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                        O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                        O H  CH.sub.3    CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                        O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                        O H  OCH.sub.3   CH.sub.3    N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 SeCH.sub.3                                                                        O H  Cl          OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                           O H  Cl          OCH.sub.3   CH 136-141             CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                           O H  OCH.sub.2 CH.sub.3                                                                        NHCH.sub.3  CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    N  117-118             CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                           O H  CH.sub.3    CH.sub.3    CH 174-176             CO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   CH 159-160             CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                          O H  CH.sub.3    OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                          O H  CH.sub.3    CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                          O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                          O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                          O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 NO.sub.2                                                                          O H  Cl          OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 NC  O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH.sub.2 NC  O H  CH.sub.3    OCH.sub.3   N                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH 132-136             CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   N                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   N(OCH.sub.3)CH.sub.                                                                       N                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   CH 160-164             CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    N  106-109             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub. 2 CN O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub.2 SCN O H  OCH.sub.3   CN          CH                     CO.sub.2 CH.sub.2 CCH                                                                      CH.sub.2 P(O) (OCH.sub.3).sub.2                                                            O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.2 F                                                               CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.2 F                                                               CH.sub.2 SCN O H  CH.sub.3    CHO         CH                     CO.sub.2 CH.sub.2 CF.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub. 2 CH.sub.2 SCH.sub.3                                                      CH.sub.2 CN  O H  OCH.sub.3   N.sub.3     CH                     CO.sub.2 CH.sub.2 CH.sub.2 SCH.sub.3                                                       CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    N                      C(O)NHCH.sub.3                                                                             CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     C(O)NHCH.sub.3                                                                             CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH                     C(O)NHCH.sub.3                                                                             CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     C(O)NHCH.sub.3                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 CN  O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     C(O)(CH.sub.3).sub.2                                                                       CH.sub.2 SCN O H  Cl          OCH.sub.3   CH                     C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     C(O)N(CH.sub. 3).sub.2                                                                     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      C(O)N(CH.sub.3).sub.2                                                                      CH.sub.2 SeCH.sub.2 CH.sub.2 CH.sub.3                                                      O H  OCH.sub.3   OCH.sub.3   CH                     C(O)N(CH.sub.3).sub.2                                                                      CHN(CH.sub.3).sub.2                                                                        O H  OCH.sub.3   CH(OCH.sub.3).sub.2                                                                       CH                     SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   N                      SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 SCN O H  Cl          OCH.sub.3   CH                     SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     SO.sub.2 NHCH.sub.3                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 NHCH.sub.2 CH.sub.3                                                               CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 NHCH.sub.2 CH.sub.3                                                               CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 NHCH.sub.2 CH.sub.3                                                               CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 NHCH.sub.2 CH.sub.3                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 NHCH.sub.2 CH.sub.2 CH.sub.3                                                      CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                        CH.sub.2 SCN O H  Cl          OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3)(CH(CH.sub.3).sub.2)                                                   CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 N(CH.sub.3)(OCH.sub.3)                                                            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3)(OCH.sub.3)                                                            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 N(CH.sub.3)(OCH.sub.3)                                                            CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3)(OCH.sub.3)                                                            CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CN  O H  CH.sub.3    OCH.sub.2 CHCH.sub.2                                                                      CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 SCN O H  OCH.sub.3   N(CH.sub.3)(CH(CH.sub.3).sub.2)                                               .           CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.2 C(CH.sub.3) CH.sub.2                                                            CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 NO.sub.2                                                                          O H  OCH.sub.3   CH.sub.2 S(CH.sub.2).sub.3                                                    CH.sub.3    N                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   (CH.sub.2).sub.4 CH.sub.2                                                     SCH.sub.2 CH.sub.3                                                                        CH                     SO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     SO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 CH.sub.3                                                                          C(O)H        O H  OCH.sub.3   OCH.sub.3   CH 166-168             SO.sub.2 CH.sub.3                                                                          CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   CH 177-175             SO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   cyclopropyl CH                     SO.sub.2 CH.sub.3                                                                          CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.3                                                                          CH.sub. 2 P(O)(OCH.sub.3).sub.2                                                            O H  CH.sub.3    OCH.sub.3   N                      SO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.3                                                                          CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   2-methylcyclo-                                                                            CH                                                                propyl                             SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.3    CCH         CH                     SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  OCH.sub. 3  cyclopentyl N                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 SCN O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH 157-158             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH 151-156             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  CH.sub.3    CH.sub.3    CH 160-162             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  Cl          OCH.sub.3   CH 151-160             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N  157-167             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N  206-208             SO.sub.2 CH.sub. 2 CH.sub.2 CH.sub.3                                                       CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   CH 164-168             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    CH 157-159             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  CH.sub.3    CH.sub.3    CH 163-166             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  Cl          OCH.sub.3   CH 182-184             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   N  176-178             SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    N  179-181             SCH.sub.3    CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     SCH.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O N  OCH.sub.3   OCH.sub.3   N                      S(O)CH.sub.2 CH.sub.3                                                                      CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     S(O)CH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N                      OSO.sub.2 CH.sub. 3                                                                        CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     OSO.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   CHO         CH                     OSO.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   CCCH.sub.3  CH                     OSO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH                     OSO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   N                      OSO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   COCH.sub.3  CH                     OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   CH(OCH.sub.3).sub.2                                                                       CH                     OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH                     OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    N                      OSO.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   CH(SCH.sub.3)(OCH.sub.2                                                       CH.sub.3)   CH                     OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     CH.sub.2 OCH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      CH.sub.2 SCH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    C(CH.sub.3)(SCH.sub.3).sub.2                                                              CH                     CH.sub.2 CH.sub.3 OCH.sub.3                                                                CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 CH.sub.2 OCH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      CH.sub.2 CH.sub.2 OCH.sub.3                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                                       CH.sub.2 CN  O H  OCH.sub.3   1,3-dioxolan-2-yl                                                                         CH                     CH.sub.2 CN  CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      C.sub.2 H.sub.5                                                                            CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     C.sub.2 H.sub.5                                                                            CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     C.sub.2 H.sub.5                                                                            CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      C.sub.2 H.sub.5                                                                            CH.sub.2 SCN O H  OCH.sub.3   2-methyl-1,3-                                                                             CH                                                                oxathion-2-yl                      COCH.sub.3   CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     COCH.sub.2 CH.sub.3                                                                        CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   N                      COCCCH.sub.3 CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     COCH.sub.2 CH.sub.2 Cl                                                                     CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     C(O)--cyclo- CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      propyl                                                                        C(O)--cyclo- CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     propyl                                                                        C(O)--cyclo- CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH                     propyl                                                                        CH(OCH.sub.3).sub.2                                                                        CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      CH(OCH.sub.3).sub.2                                                                        CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     CH(OCH.sub.2 CH.sub.3).sub.2                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     CH(OCH.sub.2 CH.sub.3).sub.2                                                               CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   CH.sub.3    CH                     1,3-dioxyl-2-yl                                                                            CH.sub.2 CN  O H  CH.sub.3    OCH.sub.3   CH                     1,3-dioxyl-2-yl                                                                            CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N                      R.sub.1A     CH.sub.2 CN  O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     R.sub.1A     CH.sub.2 CN  O H  OCH.sub.3   1,3-oxathion-2-yl                                                                         CH                     R.sub.1A     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1A     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1A     CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     R.sub.1A     CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1A     CH.sub.2 SCN O H  CH.sub.3    2-methyl-1,3-                                                                             CH                                                                dithian-2-yl                       R.sub.1A     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1A     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1A     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1B     CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     R.sub.1B     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1B     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1B     CH.sub.2 CN  O H  OCH.sub.3   4-methyl-1,3-                                                                             CH                                                                dioxolan-2-yl                      R.sub.1B     CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1B     CH.sub.2 SCN O H  Cl          OCH.sub.3   CH                     R.sub.1B     CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1B     CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   N                      R.sub.1B     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1B     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                             O H  CH.sub.3    OCH.sub.3   CH                     R.sub.1C     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1C     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1C     CH.sub.2 CN  O H  OCH.sub.3   4-methyl-1,3-                                                                             CH                                                                oxathiolan-2-yl                    R.sub.1C     CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N                      R.sub.1C     CH.sub.2 SCN O H  CH.sub.3    OCH.sub.3   CH                     R.sub.1C     CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1C     CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH                     R.sub.1C     CH.sub.2 P(O)(OMe).sub.2                                                                   O H  CH.sub.3    OCH.sub.3   CH                     R.sub.1C     CH.sub.2 P(O)(OMe).sub.2                                                                   O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1C     CH.sub.2 P(O)(OMe).sub.2                                                                   O H  CH.sub.2 CH.sub.3                                                                         OCH.sub.3   CH                     R.sub.1D     CH.sub.2 P(O)(OMe).sub.2                                                                   O H  OCH.sub.3   2,4-dimethyl-1,3-                                                                         CH                                                                dithiolan-2-yl                     R.sub.1D     CH.sub.2 P(O)(OMe).sub.2                                                                   O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1E     CH.sub.2 P(O)(OMe).sub.2                                                                   O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1F     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1G     CH.sub.2 CN  O H  OCH.sub.3   N(OCH.sub.3)CH.sub.3                                                                      CH                     R.sub.1H     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1I     CH.sub.2 CN  O H  CH.sub.3    CH.sub.3    CH                     R.sub.1J     CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1K     CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1L     CH.sub.2 SCN O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1M     CH.sub.2 SCN O H  OCH.sub.3   CH.sub.3    CH                     R.sub.1N     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1O     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1P     CH.sub.2 CN  O H  Cl          OCH.sub.3   CH                     R.sub.1Q     CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      R.sub.1R     CH.sub.2 P(O)(OMe).sub.2                                                                   O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1S     CH.sub.2 P(O)(OMe).sub.2                                                                   O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                           O H  CH.sub.3    CH.sub.3    CH 165-170             CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                           O H  Cl          OCH.sub.3   CH 146-148             CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CN  O H  Cl          OCH.sub.3   CH 104-115             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   CH 149-150             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    CH 142-144             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                           O H  Cl          OCH.sub.3   CH 161-162             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                           O H  CH.sub.3    CH.sub.3    CH 171-173             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   N  133-134             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    N  125-127             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH 138-140             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  Cl          OCH.sub.3   CH                     CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  CH.sub.3    CH.sub.3    CH 167-169             CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N                      Cl           CH(CH.sub.3)CN                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3    CHFCN        O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH(CH.sub.2 CH.sub.3)SCN                                                                   O H  CH.sub.3    CH.sub.3    CH                     NO.sub.2     CH(CH.sub.3)P(O)(OCH.sub.3).sub.2                                                          O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub. 3).sub.2                                                                CH(CH.sub.2 CH.sub.3)P(S)(CH.sub.3).sub.2                                                  O H  OCH.sub.3   CH.sub.3    N                      CO.sub.2 N(CH.sub.3).sub.2                                                                 CH(CH.sub.3)N(CH.sub.3).sub.2                                                              O H  Cl          OCH.sub.3   CH                     OCH.sub.3    CH(OC(O)CH.sub.3).sub.2                                                                    O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.3    CH(CH.sub.2 CH.sub.3)N.sub.3                                                               O H  OCH.sub.3   CH.sub.3    CH                     Cl           CH(CH.sub.3)SeCH.sub.3                                                                     O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH(CH.sub.2 CH.sub.3)N.sub.3                                                               O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                        O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                        O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                        O H  Cl          OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                        O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)N.sub.3                                                                        O H  OCH.sub.3   CH.sub.3    N                      OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)CN                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH(CH.sub.3)CN                                                                             O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.2 CH.sub. 3                                                                        CH(CH.sub.3)CN                                                                             O H  OCH.sub.3   CH.sub.3    N                      CO.sub.2 CH.sub.3                                                                          CH(CH.sub.2 CH.sub.3)NC                                                                    O H  OCH.sub.3   OCH.sub.3   CH                     Cl           CH(OCH.sub.3).sub.2                                                                        O H  OCH.sub.3   OCH.sub.3   CH                     NO.sub.2     CH(OCH.sub.3).sub.2                                                                        O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH(OCH.sub.3).sub.2                                                                        O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CH(OCH.sub.3).sub.2                                                                        O H  Cl          OCH.sub.3   CH                     OCH.sub.3    CH(OCH.sub.3).sub.2                                                                        O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.3    CH(OCH.sub.3).sub.2                                                                        O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         CH(OCH.sub.3).sub.2                                                                        O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          CH(OCH.sub.3).sub.2                                                                        O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH(OCH.sub.3).sub.2                                                                        O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH(OCH.sub.3).sub.2                                                                        O H  OCH.sub.3   CH.sub.3    N                      CO.sub.2 CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.3).sub.2                                                               O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  CH.sub.3    CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  Cl          OCH.sub.3   CH                     OCH.sub.3    C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)(OCH.sub.3).sub.2                                                               O H  CH.sub.3    CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          C(CH.sub.2 CH.sub.3)(OCH.sub.3).sub.2                                                      O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          CH(SCH.sub.3).sub.3                                                                        O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          C(CH.sub.2 CH.sub.3)(SCH.sub.3).sub. 2                                                     O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                                       O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3                                                                                   ##STR22##   O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH(CN)(OSi(CH.sub.3).sub.3)                                                                O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          CH(CN)(OSi(CH.sub.3).sub.3)                                                                O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          C(CH.sub.3)(CN)OH                                                                          O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          C(CH.sub.2 CH.sub.3)(CN)OCH.sub.3                                                          O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          1,-3-dithiolan-2-yl                                                                        O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          1,-3-dithiolan-2-yl                                                                        O H  Cl          OCH.sub.3   CH                     Cl           1,-3-dithiolan-2-yl                                                                        O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                         O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                         O H  OCH.sub.3   CH.sub.3    CH                     NO.sub.2     1,-3-dioxolan-2-yl                                                                         O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          2-methyl-1,3-                                                                              O H  OCH.sub.3   OCH.sub.3   CH                                  dioxolan-2-yl                                                    CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                         O H  OCH.sub. 3  OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                         O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                          1,-3-dioxolan-2-yl                                                                         O H  Cl          OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 1,-3-dithian-2-yl                                                                          O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                          2-methyl-1,3-                                                                              O H  OCH.sub.3   OCH.sub.3   CH                                  dioxan-2-yl                                                      C.sub.6 H.sub.5                                                                            CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH                     Cl                                                                                          ##STR23##   O H  OCH.sub.3   OCH.sub.3   CH                     NO.sub.2                                                                                    ##STR24##   O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                  ##STR25##   O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3                                                                                   ##STR26##   O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.3                                                                                   ##STR27##   O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.3                                                                                   ##STR28##   O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                          ##STR29##   O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                          ##STR30##   O H  OCH.sub.3   OCH.sub.3   CH 192-192             OCH.sub.2 CH.sub.3                                                                          ##STR31##   O H  OCH.sub.3   CH.sub.3    N  188-190             OCH.sub.2 CH.sub.3                                                                          ##STR32##   O H  CH.sub.3    CH.sub.3    CH 180-181             OCH.sub.2 CH.sub.3                                                                          ##STR33##   O H  OCH.sub.3   CH.sub.3    CH 137-138             OCH.sub.2 CH.sub.3                                                                          ##STR34##   O H  Cl          OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                          ##STR35##   O H  OCH.sub.3   OCH.sub.3   N  135-136             OCH.sub.2 CH.sub.3                                                                          ##STR36##   O H  OCH.sub.3   OCH.sub.3   CH                     OCH.sub.2 CH.sub.3                                                                          ##STR37##   O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CH.sub.3                                                                          ##STR38##   O H  Cl          OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                           ##STR39##   O H  OCH.sub.3   OCH.sub.3   CH 189-190             CO.sub.2 CH.sub.3                                                                           ##STR40##   O H  OCH.sub.3   CH.sub.3    CH 115                 CO.sub.2 CH.sub.3                                                                           ##STR41##   O H  Cl          OCH.sub.3   CH 182-184             CO.sub.2 CH.sub.3                                                                           ##STR42##   O H  OCH.sub.3   OCH.sub.3   N  174-175             CO.sub.2 CH.sub.3                                                                           ##STR43##   O H  OCH.sub.3   CH.sub.3    N  150-154             CO.sub.2 CH.sub.3                                                                           ##STR44##   O H  CH.sub.3    CH.sub.3    CH 145-147             CO.sub.2 CH.sub.3                                                                           ##STR45##   O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.3                                                                           ##STR46##   O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.3                                                                           ##STR47##   O H  OCH.sub.3   OCH.sub.3   N                      CO.sub.2 CH.sub.3                                                                           ##STR48##   O H  OCH.sub.3   CH.sub.3    N                      CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR49##   O H  OCH.sub.3   OCH.sub.3   CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR50##   O H  OCH.sub.3   CH.sub.3    CH                     CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR51##   O H  Cl          OCH.sub.3   CH 123-124             OSO.sub.2 CH.sub.3                                                                          ##STR52##   O H  OCH.sub.3   CH.sub.3    CH                     SO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR53##   O H  OCH.sub.3   OCH.sub.2 CH.sub.3                                                                        CH                     C(O)N(CH.sub.2 CH.sub.3).sub.2                                                             Cl           O H  CH.sub.3    CH.sub.3    CH 180-183             Cl           CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   CH 150-152             Cl           CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    CH 138-139             Cl           CH.sub.2 N.sub.3                                                                           O H  CH.sub.3    CH.sub.3    CH 167-170             Cl           CH.sub.2 N.sub.3                                                                           O H  Cl          OCH.sub.3   CH 145-147             Cl           CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   N  134-137             Cl           CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    N  oil                 CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR54##   O H  OCH.sub.3   OCH.sub.3   CH 144-146             CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR55##   O H  CH.sub.3    CH.sub.3    CH 144-146             CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR56##   O H  OCH.sub.3   OCH.sub.3   N  146-148             CO.sub.2 CH.sub.2 CH.sub.3                                                                  ##STR57##   O H  OCH.sub.3   CH.sub.3    N  142-145             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   CH 128                 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    CH 131-132             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  CH.sub.3    CH.sub.3    CH 144-147             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  Cl          OCH.sub.3   CH 156-158             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   OCH.sub.3   N  134-135             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 N.sub.3                                                                           O H  OCH.sub.3   CH.sub.3    N  oil                 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   CH 130-131             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    CH 144-145             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  CH.sub.3    CH          CH.sub.3                                                                         150-152             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  Cl          OCH.sub.3   CH 178-181             CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   OCH.sub.3   N  oil                 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.2 CN  O H  OCH.sub.3   CH.sub.3    N  oil                 CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH 171-174             CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   CH.sub.3    CH 188-190             CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  CH.sub.3    CH.sub.3    CH 182-185             CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  Cl          OCH.sub.3   CH 185-188             CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   N  167-169             CO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   CH.sub.3    N  136-138             OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                             O H  OCH.sub. 3  OCH.sub.3   CH 170-171             OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   CH.sub.3    CH 183-185             OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                             O H  CH.sub.3    CH.sub.3    CH 180-182             OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                             O H  Cl          OCH.sub.3   CH 115-118             OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   N  95-100              OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   CH.sub.3    N  112-116             OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH 185-187             OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   CH.sub.3    CH                     OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   N                      OCH.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   CH.sub.3    N                      F            CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     F            CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     F            C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     F            C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub. 3  CH                     Cl           CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     Cl           CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     Cl           C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     Cl           C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     NO.sub.2     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     NO.sub.2     CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     NO.sub.2     C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     NO.sub.2     C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.3     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.3     CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.3     C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.3     C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     C(O)N(CH.sub.3).sub.2                                                                      CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     C(O)N(CH.sub.3).sub.2                                                                      CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     C(O)N(CH.sub.3).sub.2                                                                      C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     C(O)N(CH.sub.3).sub.2                                                                      C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 N(CH.sub.3).sub.2                                                                 C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.3                                                                          CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.3                                                                          CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.3                                                                          C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     SO.sub.2 CH.sub.3                                                                          CH(CH.sub.3)NOCH.sub.3                                                                     O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.3                                                                         CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.3                                                                         CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     OSO.sub.2 CH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 OCH.sub.3                                                                         CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 OCH.sub.3                                                                         CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 OCH.sub.3                                                                         C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 OCH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 SCH.sub.3                                                                         CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 SCH.sub.3                                                                         CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 SCH.sub.3                                                                         C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 SCH.sub.3                                                                         C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 CN  CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 CN  CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 CN  C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     CH.sub.2 CN  C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     CH(OCH.sub.3).sub.2                                                                        CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     CH(OCH.sub.3).sub.2                                                                        CHNOCH.sub.3 O H  OCH.sub.3   OCH.sub.3   CH                     CH(OCH.sub.3).sub.2                                                                        C(CH.sub.3)NOH                                                                             O H  OCH.sub.3   OCH.sub.3   CH                     CH(OCH.sub.3).sub.2                                                                        C(CH.sub.3)NOCH.sub.3                                                                      O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1A     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1B     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1C     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1D     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1E     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1F     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1G     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1H     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1I     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1J     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1K     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1L     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1M     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1N     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1O     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1P     CH NOH       O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1Q     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1R     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     R.sub.1S     CHNOH        O H  OCH.sub.3   OCH.sub.3   CH                     __________________________________________________________________________

                  TABLE II                                                        ______________________________________                                        General Formula II                                                                                                    m.p.                                  R.sub.1   R.sub.2         X.sub.1  Y.sub.1                                                                            (°C.)                          ______________________________________                                        F         CH.sub.2 CN     CH.sub.3 O                                          Cl.sub.3  CH.sub.2 SCN    OCH.sub.3                                                                              O                                          CF.sub.3  CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                       OCH.sub.3                                                                              CH.sub.2                                   NO.sub.2  CH.sub.2 CN     OCH.sub.3                                                                              O                                          OCH.sub.3 CH.sub.2 CN     OCH.sub.3                                                                              O                                          OCH.sub.3 CH.sub.2 SCN    OCH.sub.3                                                                              CH.sub.2                                   OCH.sub.2 CH.sub.3                                                                      CH.sub.2 SCN    OCH.sub.3                                                                              O                                          OCH.sub.2 CH.sub.3                                                                      CH.sub.2 CN     OCH.sub.3                                                                              CH.sub.2                                   CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN     OCF.sub.2 H                                                                            O                                          CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN     OCH.sub.3                                                                              CH.sub.2                                   CO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN    OCH.sub.3                                                                              O                                          CO.sub.2 CH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                                                              O                                          CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                                                              O                                          CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN     OCH.sub.3                                                                              CH.sub.3                                   CO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 CN     CH.sub.3 O                                          SO.sub.2 NHCH.sub.3                                                                     CH.sub. 2 CN    OCH.sub.3                                                                              O                                          SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 CN     OCH.sub.3                                                                              CH.sub.2                                   SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 SCN    OCH.sub.3                                                                              O                                          SO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN    OCH.sub.3                                                                              O                                          SO.sub.2 CH.sub.3                                                                       CH.sub.2 CN     OCF.sub.2 H                                                                            CH.sub.2                                   SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN     OCH.sub.3                                                                              O                                          SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                                                              O                                          OSO.sub.2 CH.sub.3                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                                                              CH.sub.2                                   OSO.sub.2 CH.sub.3                                                                      CH.sub.2 CN     OCH.sub.2 C                                                                            O                                          OSO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 SCN    OCH.sub.3                                                                              O                                          R.sub.1 --A                                                                             CH.sub.2 CN     CH.sub.3 O                                          R.sub.1 --A                                                                             CH.sub.2 SCN    OCH.sub.3                                                                              CH.sub.2                                   R.sub.1 --B                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                                                              O                                          R.sub.1 --C                                                                             CH.sub.2 CN     OCH.sub.3                                                                              O                                          F         CH═NOH      CH.sub.3 O                                          OCH.sub.3 CH═NOH.sub.3                                                                              OCH.sub.3                                                                              O                                          COOCH.sub.3                                                                             C(CH.sub.3)═NOH                                                                           OCF.sub.2 H                                                                            CH.sub.2                                   CO.sub.2 N(CH.sub.3).sub.2                                                              C(CH.sub.3)═NOCH.sub.3                                                                    CH.sub.3 O                                          SO.sub. 2 N(CH.sub.3).sub.2                                                             CH═NOH      OCH.sub.3                                                                              O                                          SO.sub.2 CH.sub.3                                                                       CH═NOCH.sub.3                                                                             OCH.sub.3                                                                              CH.sub.2                                   OSO.sub.2 CH.sub.2 CH.sub.3                                                             C(CH.sub.3)═NOH                                                                           OCF.sub.2 H                                                                            O                                          R.sub.1 --A                                                                             C(CH.sub.3)═NOCH.sub.3                                                                    CH.sub.3 O                                          R.sub.1 --B                                                                             CH═NOH      CH.sub.3 CH.sub.2                                   R.sub.1 --C                                                                             CH═NOCH.sub.3                                                                             OCH.sub.3                                                                              O                                          ______________________________________                                    

                  TABLE III                                                       ______________________________________                                        General Formula III                                                           R.sub.1   R.sub.2         X.sub.1   m.p. (°C.)                         ______________________________________                                        F         CH.sub.2 CN     CH.sub.3                                            Cl        CH.sub.2 SCN    OCH.sub.3                                           CF.sub.3  CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                       OCH.sub.3                                           NO.sub.2  CH.sub.2 CN     OCH.sub.3                                           OCH.sub.3 CH.sub.2 CN     OCH.sub.3                                           OCH.sub.3 CH.sub.2 SCN    OCH.sub.3                                           OCH.sub.2 CH.sub.3                                                                      CH.sub.2 SCN    OCH.sub.3                                           OCH.sub.2 CH.sub.3                                                                      CH.sub.2 CN     OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN     OCF.sub.2 H                                         CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN     OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN    OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN     OCH.sub.3                                           CO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 CN     CH.sub.3                                            SO.sub.2 NHCH.sub.3                                                                     CH.sub.2 CN     OCH.sub.3                                           SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 CN     OCH.sub.3                                           SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 SCN    OCH.sub.3                                           SO.sub.2 CH.sub. 3                                                                      CH.sub.2 SCN    OCH.sub.3                                           SO.sub.2 CH.sub.3                                                                       CH.sub.2 CN     OCF.sub.2 H                                         SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN     OCH.sub.3                                           SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                           OSO.sub.2 CH.sub.3                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                           OSO.sub.2 CH.sub.3                                                                      CH.sub.2 CN     OCH.sub.2 CH.sub.3                                  OSO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 SCN    OCH.sub.3                                           R.sub.1 --A                                                                             CH.sub.2 CN     CH.sub.3                                            R.sub.1 --A                                                                             CH.sub.2 SCN    OCH.sub.3                                           R.sub.1 --B                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                           R.sub.1 --C                                                                             CH.sub.2 CN     OCH.sub.3                                           F         CH═NOH      CH.sub.3                                            OCH.sub.3 CH═NOCH.sub.3                                                                             OCH.sub.3                                           COOCH.sub.3                                                                             C(CH.sub.3)═NOH                                                                           OCH.sub.3                                           CO.sub.2 N(CH.sub.3).sub.2                                                              C(CH.sub.3)═NOCH.sub.3                                                                    OCF.sub.2 H                                         SO.sub.2 N(CH.sub.3).sub.2                                                              CH═NOH      CH.sub.3                                            SO.sub.2 CH.sub.3                                                                       CH═NOCH.sub.3                                                                             OCH.sub.3                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                             C(CH.sub.3)═NOH                                                                           CH.sub.3                                            R.sub.1 --A                                                                             C(CH.sub.3)═NOCH.sub.3                                                                    OCH.sub.3                                           R.sub.1 --B                                                                             CH═NOH      OCF.sub.2 H                                         R.sub. 1 --C                                                                            CH═NOCH.sub.3                                                                             OCH.sub.3                                           ______________________________________                                    

                  TABLE IV                                                        ______________________________________                                        General Formula IV                                                                                                    m.p.                                  R.sub.1   R.sub.2        X.sub.1   Y.sub.3                                                                            (°C.)                          ______________________________________                                        F         CH.sub.2 CN    CH.sub.3  H                                          Cl        CH.sub.2 SCN   OCH.sub.3 H                                          CF.sub.3  CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                      OCH.sub.3 CH.sub.3                                   NO.sub.2  CH.sub.2 CN    OCH.sub.3 H                                          OCH.sub.3 CH.sub.2 CN    OCH.sub.3 H                                          OCH.sub.3 CH.sub.2 SCN   OCH.sub.3 CH.sub.3                                   OCH.sub.2 CH.sub.3                                                                      CH.sub.2 SCN   OCH.sub.3 H                                          OCH.sub.2 CH.sub.3                                                                      CH.sub.2 CN    OCH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCF.sub.2 H                                                                             H                                          CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN   OCH.sub.3 H                                          CO.sub.2 CH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               OCH.sub.3 H                                          CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               OCH.sub.3 H                                          CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN    OCH.sub.3 CH.sub.3                                   CO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 CN    CH.sub.3  H                                          SO.sub.2 NHCH.sub.3                                                                     CH.sub.2 CN    OCH.sub.3 H                                          SO N(CH.sub.3).sub.2                                                                    CH.sub.2 CN    OCH.sub.3 H                                          SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 SCN   OCH.sub.3 H                                          SO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN   OCH.sub.3 H                                          SO.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCF.sub.2 H                                                                             CH.sub.3                                   SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN    OCH.sub.3 H                                          SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               OCH.sub.3 H                                          OSO.sub.2 CH.sub.3                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               OCH.sub.3 CH.sub.3                                   OSO.sub.2 CH.sub.3                                                                      CH.sub.2 CN    OCH.sub.2 CH.sub.3                                                                      H                                          OSO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 SCN   OCH.sub.3 H                                          R.sub.1 --A                                                                             CH.sub.2 CN    CH.sub.3  H                                          R.sub.1 --A                                                                             CH.sub.2 SCN   OCH.sub.3 CH.sub.3                                   R.sub.1 --B                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               OCH.sub.3 H                                          R.sub.1 --C                                                                             CH.sub.2 CN    OCH.sub.3 H                                          F         CH═NOH     CH.sub.3  H                                          OCH.sub.3 CH═NOH.sub.3                                                                             CH.sub.3  CH.sub.3                                   COOCH.sub.3                                                                             C(CH.sub.3)═NOH                                                                          OCH.sub.3 H                                          CO.sub.2 N(CH.sub.3).sub.2                                                              C(CH.sub.3)═NOCH.sub.3                                                                   OCH.sub.3 H                                          SO.sub.2 N(CH.sub.3 ).sub.2                                                             CH═NOH     CH.sub.3  H                                          SO.sub.2 CH.sub.3                                                                       CH═NOCH.sub.3                                                                            CH.sub.3  CH.sub.3                                   OSO.sub.2 CH.sub.2 CH.sub.3                                                             C(CH.sub.3)═NOH                                                                          CH.sub.3  H                                          R.sub.1 --A                                                                             C(CH.sub.3)═NOCH.sub.3                                                                   OCH.sub.3 H                                          R.sub.1 --B                                                                             CH═NOH     CH.sub.3  CH.sub.3                                   R.sub.1 --C                                                                             CH═NOCH.sub.3                                                                            OCH.sub.3 H                                          ______________________________________                                    

                                      TABLE V                                     __________________________________________________________________________    General Formula V                                                             R.sub.1 R.sub.2    X.sub.2                                                                            Y.sub.2                                                                             m.p. (°C.)                               __________________________________________________________________________    F       CH.sub.2 CN                                                                              CH.sub.3                                                                           OCH.sub.3                                             Cl      CH.sub.2 SCN                                                                             CH.sub.3                                                                           OCH.sub.2 CH.sub.3                                    CF.sub.3                                                                              CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                  CH.sub.3                                                                           OCH.sub.3                                             NO.sub.2                                                                              CH.sub.2 CN                                                                              CH.sub.3                                                                           SCH.sub.3                                             OCH.sub.3                                                                             CH.sub.2 CN                                                                              CH.sub.2 CH.sub.3                                                                  OCH.sub.3                                             OCH.sub.3                                                                             CH.sub.2 SCN                                                                             CH.sub.3                                                                           SCH.sub.2 CH.sub.3                                    OCH.sub.2 CH.sub.3                                                                    CH.sub.2 SCN                                                                             CH.sub.3                                                                           OCH.sub.3                                             OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CN                                                                              CH.sub.2 CF.sub.3                                                                  OCH.sub.3                                             CO.sub.2 CH.sub.3                                                                     CH.sub.2 CN                                                                              CH.sub.3                                                                           CH.sub.3                                              CO.sub.2 CH.sub.3                                                                     CH.sub.2 CN                                                                              CH.sub.3                                                                           OCH.sub.3                                             CO.sub.2 CH.sub.3                                                                     CH.sub.2 SCN                                                                             CH.sub.3                                                                           CH.sub.2 CH.sub.3                                     CO.sub.2 CH.sub.3                                                                     CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           CH.sub.2 CH.sub.3                                                                  OCH.sub.3                                             CO.sub.2 CH.sub.2 CH.sub.3                                                            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           CH.sub.3                                                                           OCH.sub.3                                             CO.sub.2 CH.sub.2 CH.sub.3                                                            CH.sub.2 CN                                                                              CH.sub.3                                                                           OCH.sub.2 CH.sub.3                                    CO.sub.2 N(CH.sub.3).sub.2                                                            CH.sub.2 CN                                                                              CH.sub.2 CF.sub.3                                                                  OCH.sub.3                                             SO.sub.2 NHCH.sub.3                                                                   CH.sub.2 CN                                                                              CH.sub.3                                                                           OCH.sub.3                                             SO.sub.2 N(CH.sub.3).sub.2                                                            CH.sub.2 CN                                                                              CH.sub.3                                                                           SCH.sub.3                                             SO.sub.2 N(CH.sub.3).sub.2                                                            CH.sub.2 SCN                                                                             CH.sub.2 CH.sub.3                                                                  OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                     CH.sub.2 SCN                                                                             CH.sub.3                                                                           OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                     CH.sub.2 CN                                                                              CH.sub.3                                                                           SCH.sub.2 CH.sub.3                                    SO.sub.2 CH.sub.2 CH.sub.3                                                            CH.sub.2 CN                                                                              CH.sub.3                                                                           OCH.sub.3                                             SO.sub.2 CH.sub.2 CH.sub.3                                                            CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           CH.sub.2 CF.sub.3                                                                  OCH.sub.3                                             OSO.sub.2 CH.sub.3                                                                    CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           CH.sub.3                                                                           CH.sub.3                                              OSO.sub.2 CH.sub.3                                                                    CH.sub.2 CN                                                                              CH.sub.3                                                                           OCH.sub.3                                             OSO.sub.2 CH.sub.2 CH.sub.3                                                           CH.sub.2 SCN                                                                             CH.sub.2 CH.sub.3                                                                  OCH.sub.3                                             R.sub.1 --A                                                                           CH.sub.2 CN                                                                              CH.sub.3                                                                           OCH.sub.3                                             R.sub.1 --A                                                                           CH.sub.2 SCN                                                                             CH.sub.3                                                                           CH.sub.2 CH.sub.3                                     R.sub.1 --B                                                                           CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           CH.sub.3                                                                           OCH.sub.3                                             R.sub.1 --C                                                                           CH.sub.2 CN                                                                              CH.sub.3                                                                           OCH.sub.3                                             F       CH═NOH CH.sub. 3                                                                          OCH.sub.3                                             OCH.sub.3                                                                             CH═NOHCH.sub.3                                                                       CH.sub.3                                                                           CH.sub.3                                              COOCH.sub.3                                                                           C(CH.sub.3)═NOH                                                                      CH.sub.2 CH.sub.3                                                                  OCH.sub.3                                             CO.sub.2 N(CH.sub.3).sub.2                                                            C(CH.sub.3)═NOCH.sub.3                                                               CH.sub.2 CF.sub.3                                                                  CH.sub.3                                              SO.sub.2 N(CH.sub.3).sub.2                                                            CH═NOH CH.sub.3                                                                           OCH.sub.2 CH.sub.3                                    SO.sub.2 CH.sub.3                                                                     CH═NOCH.sub.3                                                                        CH.sub.3                                                                           OCH.sub.3                                             OSO.sub.2 CH.sub.2 CH.sub.3                                                           C(CH.sub.3)═NOH                                                                      CH.sub.2 CF.sub.3                                                                  OCH.sub.3                                             R.sub.1 --A                                                                           C(CH.sub.3)═NOCH.sub.3                                                               CH.sub.2 CH.sub.3                                                                  CH.sub.3                                              R.sub.1 --B                                                                           CH═NOH CH.sub.3                                                                           OCH.sub.3                                             R.sub.1 --C                                                                           CH═NOCH.sub.3                                                                        CH.sub.3                                                                           CH.sub.3                                              __________________________________________________________________________

                  TABLE VI                                                        ______________________________________                                        General Formula VI                                                            R.sub.1   R.sub.2         X.sub.3  m.p. (°C.)                          ______________________________________                                        F         CH.sub.2 CN     OCH.sub.3                                           Cl        CH.sub.2 SCN    OCH.sub.3                                           CF.sub.3  CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                       OCH.sub.3                                           NO.sub.2  CH.sub.2 CN     CH.sub.3                                            OCH.sub.3 CH.sub.2 CN     OCH.sub.3                                           OCH.sub.3 CH.sub.2 SCN    CH.sub.3                                            OCH.sub.2 CH.sub.3                                                                      CH.sub.2 SCN    OCH.sub.3                                           OCH.sub.2 CH.sub.3                                                                      CH.sub.2 CN     CH.sub.3                                            CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN     OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN     CH.sub.3                                            CO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN    OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                CH.sub.3                                            CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN     CH.sub.3                                            CO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 CN     OCH.sub.3                                           SO.sub.2 NHCH.sub.3                                                                     CH.sub.2 CN     CH.sub.3                                            SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 CN     OCH.sub.3                                           SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 SCN    CH.sub.3                                            SO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN    OCH.sub.3                                           SO.sub.2 CH.sub.3                                                                       CH.sub.2 CN     OCH.sub.3                                           SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN     CH.sub.3                                            SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                OCH.sub.3                                           OSO.sub.2 CH.sub.3                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                CH.sub.3                                            OSO.sub.2 CH.sub.3                                                                      CH.sub.2 CN     OCH.sub.3                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 SCN    OCH.sub.3                                           R.sub.1 --A                                                                             CH.sub.2 CN     CH.sub.3                                            R.sub.1 --A                                                                             CH.sub.2 SCN    OCH.sub.3                                           R.sub.1 --B                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                                CH.sub.3                                            R.sub.1 --C                                                                             CH.sub.2 CN     OCH.sub.3                                           F         CH═NOH      OCH.sub.3                                           OCH.sub.3 CH═NOCH.sub.3                                                                             OCH.sub.3                                           COOCH.sub.3                                                                             C(CH.sub.3)═NOH                                                                           CH.sub.3                                            CO.sub.2 N(CH.sub.3).sub.2                                                              C(CH.sub.3)═NOCH.sub.3                                                                    CH.sub.3                                            SO.sub.2 CH.sub.3                                                                       CH═NOH      OCH.sub.3                                           OSO.sub.2 CH.sub.2 CH.sub.3                                                             C(CH.sub.3)═NOCH.sub.3                                                                    OCH.sub.3                                           R.sub.1 --A                                                                             C(CH.sub.3)═NOH                                                                           OCH.sub.3                                           R.sub.1 --B                                                                             C(CH.sub.3)═NOCH.sub.3                                                                    CH.sub.3                                            R.sub.1 --C                                                                             CH═NOH      OCH.sub.3                                           ______________________________________                                    

                  TABLE VII                                                       ______________________________________                                        General Formula VII                                                           R.sub.1   R.sub.2        X.sub.4   Y.sub.4 m.p. (°C.)                  ______________________________________                                        F         CH.sub.2 CN    CH.sub.3  OCH.sub.3                                  Cl        CH.sub.2 SCN   OCH.sub.3 CH.sub.3                                   CF.sub.3  CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2                                                      OCH.sub.2 CH.sub.3                                                                      OCH.sub.3                                  NO.sub.2  CH.sub.2 CN    CH.sub.2 OCH.sub.3                                                                      OCH.sub.3                                  OCH.sub.3 CH.sub.2 CN    Cl        OCH.sub.3                                  OCH.sub.3 CH.sub.2 SCN   CH.sub.3  OCH.sub.2 CH.sub.3                         OCH.sub.2 CH.sub.3                                                                      CH.sub.2 SCN   OCH.sub.3 OCH.sub.3                                  OCH.sub.2 CH.sub.3                                                                      CH.sub.2 CN    OCH.sub.3 Cl                                         CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN    CH.sub.3  OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCH.sub.3 OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN   OCH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.3                                                                       CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               OCH.sub.2 CH.sub.3                                                                      OCH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               OCH.sub.3 OCH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN    OCH.sub.3 OCH.sub.2 CH.sub.3                         CO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub. 2 CN   CH.sub.2 OCH.sub.3                                                                      OCH.sub.3                                  SO.sub.2 NHCH.sub.3                                                                     CH.sub.2 CN    OCH.sub.3 CH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 CN    OCH.sub.3 OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                              CH.sub.2 SCN   Cl        OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                       CH.sub.2 SCN   OCH.sub.3 CH.sub.3                                   SO.sub.2 CH.sub.3                                                                       CH.sub.2 CN    OCH.sub.3 OCH.sub.3                                  SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 CN    OCH.sub.3 OCH.sub.3                                  SO.sub.2 CH.sub.2 CH.sub.3                                                              CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               CH.sub.3  OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                      CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               OCH.sub.3 OCH.sub.2 CH.sub.3                         OSO.sub.2 CH.sub.3                                                                      CH.sub.2 CN    OCH.sub.3 OCH.sub.3                                  OSO.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 SCN   OCH.sub.2 CH.sub.3                                                                      OCH.sub.3                                  R.sub.1 --A                                                                             CH.sub.2 CN    OCH.sub.3 OCH.sub.3                                  R.sub.1 --A                                                                             CH.sub.2 SCN   OCH.sub.3 CH.sub.3                                   R.sub.1 --B                                                                             CH.sub.2 P(O)(OCH.sub.3).sub.2                                                               CH.sub.2 OCH.sub.3                                                                      OCH.sub.3                                  R.sub.1 --C                                                                             CH.sub.2 CN    OCH.sub.3 OCH.sub.3                                  F         CH═NOH     CH.sub.3  OCH.sub.3                                  OCH.sub.3 CH═NOCH.sub.3                                                                            OCH.sub.3 CH.sub.3                                   COOCH.sub.3                                                                             C(CH.sub.3)═NOH                                                                          OCH.sub.2 CH.sub.3                                                                      OCH.sub.3                                  CO.sub.2 N(CH.sub.3).sub.2                                                              C(CH.sub.3)═NOCH.sub.3                                                                   CH.sub.2 OCH.sub.3                                                                      OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                       CH═NOH.sub.3                                                                             Cl        OCH.sub.3                                  OSO.sub.2 CH.sub.2 CH.sub.3                                                             C(CH.sub.3)═NOCH.sub.3                                                                   CH.sub.3  OCH.sub.2 CH.sub.3                         R.sub.1 --A                                                                             C(CH.sub.3)═NOH                                                                          OCH.sub.3 OCH.sub.3                                  R.sub.1 --B                                                                             CH(CH.sub.3)═NOCH.sub.3                                                                  OCH.sub.3 Cl                                         R.sub.1 --C                                                                             CH═NOH     CH.sub.3  OCH.sub.3                                  ______________________________________                                    

FORMULATIONS

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solution,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

    ______________________________________                                                    Weight Percent*                                                               Active                                                                        Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, N.Y.,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growthk, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solids compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182; H. Gysin and E. Knusli,U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5,line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 10

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        5-(cyanomethyl)-2-methoxy-N--[(4-methoxy-                                                                 99%                                               6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-                                   benzenesulfonamide                                                            trimethylnonyl polyethylene glycol ether                                                                   1%                                               ______________________________________                                    

The surfactant is sprayed upon the active ingredient in a blender andthe mixture sifted through a U.S.S. no. 40 sieve (0.42 mm openings)prior to packaging. The concentrate may be formulated further forpractical use.

EXAMPLE 11

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin-                                                              65%                                               2-yl)aminocarbonyl]-2-methoxybenzene-                                         sulfonamide                                                                   dodecylphenol polyethylene glycol ether                                                                    2%                                               sodium ligninsulfonate       4%                                               sodium silicoaluminate       6%                                               montmorillonite (calcined)  23%                                               ______________________________________                                    

The ingredients are thoroughly blended. The liquid surfactant is addedby spraying upon the solid ingredients in the blender. After grinding ahammer mill to produce particles essentially all below 100 microns, thematerial is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mmopening) and packaged.

EXAMPLE 12

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        5-(cyanomethyl)-2-methoxy-N--[(4-methoxy-                                                                50.0%                                              6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-                                   benzenesulfonamide                                                            polyacrylic acid thickener 0.3%                                               dodecylphenol polyethylene glycol ether                                                                  0.5%                                               disodium phosphate         1%                                                 monosodium phosphate       0.5%                                               polyvinyl alcohol          1.0%                                               water                      56.7%                                              ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 13

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        5-(cyanomethyl)-2-methoxy-N--[(4-methoxy-                                                                 35%                                               6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-                                   benzenesulfonamide                                                            blend of polyalcohol carboxylic esters                                                                     6%                                               and oil soluble petroleum sulfonates                                          xylene                      59%                                               ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 3 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 14

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin                                                               25%                                               2-yl)aminocarbonyl]-2-methoxybenzene-                                         sulfonamide.                                                                  polyoxyethylene sorbitol hexaoleate                                                                        5%                                               highly aliphatic hydrocarbon oil                                                                          70%                                               ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 15

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin-                                                              25%                                               2-yl)-aminocarbonyl]-2-methoxybenzene-                                        sulfonamide                                                                   hydrated attapulgite        3%                                                crude calcium ligninsulfonate                                                                             10%                                               sodium dihydrogen phosphate 0.5%                                              water                       61.5%                                             ______________________________________                                    

The ingredients are ground together in a ball or roller mill until thesolid particles have been reduced to diameters under 10 microns.

EXAMPLE 16

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        5-(cyanomethyl)-2-methoxy-N[(4-methoxy-                                                                   40%                                               6-methyl-1,3,5-triazin-2-yl)amino-                                            carbonyl]benzenesulfonamide                                                   dioctyl sodium sulfosuccinate                                                                             1.5%                                              sodium ligninsulfonate      3%                                                low viscosity methyl cellulose                                                                            1.5%                                              attapulgite                 54%                                               ______________________________________                                    

The ingredients are thoroughly blende, passed thrugh an air mill, toproduce an average particle size under 15 microns, reblended, and siftedthrough a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

All compounds of the invention may be formulated in the same manner.

EXAMPLE 17

    ______________________________________                                        Granule                                                                       ______________________________________                                        wettable powder of Example 16                                                                           15%                                                 gypsum                    69%                                                 potassium sulfate         16%                                                 ______________________________________                                    

The ingredients are blended in a rotating mixer and water sprayed on toaccomplish granulation. When most of the material has reached thedesired range of 1.0 to 0.42 cm (U.S.S. #18 to 40 sieves), the granulesare removed, dried, and screened. Oversized material is crushed toproduce additional material in the desired range. These granules contain% active ingredient.

EXAMPLE 18

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        5-(cyanomethyl)-N--[(4,6-diemthoxyprimidin-                                                               50%                                               2-yl)-aminocarbonyl]-2-methoxybenzene-                                        sulfonamide                                                                   sodium alkylnaphthalenesulfonate                                                                           2%                                               low viscosity methyl cellulose                                                                             2%                                               diatomaceous earth          46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammermilled and the air milled toproduce particles of active essentially all below 10 microns indiameter. The product is reblended before packaging.

EXAMPLE 19

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin-                                                              25%                                               2-yl)aminocarbonyl]-2-methoxybenzene-                                         sulfonamide                                                                   anhydrous sodium sulfate    10%                                               crude calcium ligninsulfonate                                                                              5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite 59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 20

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        5-(cyanomethyl)-2-methoxy-N--[(4-methoxy-6-                                                             80%                                                 methyl-1,3,5-triazin-2-yl)aminocarbonyl]-                                     benzenesulfonamide                                                            sodium alkylnaphthalenesulfonate                                                                        2%                                                  sodium ligninsulfonate    2%                                                  synthetic amorphous silica                                                                              3%                                                  kaolinite                 13%                                                 ______________________________________                                    

The ingredients are blended and then ground in a hammermill to produceparticles with an average particle size less than 25 microns indiameter. The material is reblended and sifted through a U.S.S. No. 50sieve (0.3 mm opening) before being packaged.

EXAMPLE 21

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin-                                                            98.5%                                               2-yl)-aminocarbonyl]-2-methoxybenzene-                                        sulfonamide                                                                   silica aerogel            0.5%                                                synthetic amorphous fine silica                                                                         1.0%                                                ______________________________________                                    

The ingredients are blended and ground in a hammer mill to produce ahigh strength concentrate essentially all passing a U.S.S. No. 50 sieve(0.3 mm openings). This material may then be formulated in a variety ofways.

UTILITY

Test results indicate that the compounds of the present invention arehighly active preemergent or postemergent herbicides or plant growthregulants. Many of them have utility for broad-spectrum pre- and/orpost-emergence weed control in areas where complete control of allvegetation is desired, such as around fuel storage tanks, ammunitiondepots, industrial storage areas, parking lots, drive-in theaters,around billboards, highway and railroad structures. Some of thecompounds have utility for selective weed control in crops such aswheat. Alternatively, the subject compounds are useful to modify plantgrowth.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as plant growthmodifiers or as herbicides, the crop species involved, the types ofweeds to be controlled, weather and climate, formulations selected, modeof application, amount of foliage pre-sent, etc. In generaly terms, thesubject compounds should be applied at levels of around 0.001 to 10kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for plant growth modificationor for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide; examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

TEST A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), cheatgrass (Bromus Secalinus), giant foxtail (Setariafaberii), wild oats (Avena fatua), velvetleaf (Aubutilon theophrasti),moringglory (Ipomoea spp., cocklebur (Xanthium pensylvanicum), sorghum,corn, barley, soybean, sugarbeet, cotton, rice, wheat and purplenutsedge (Cyperus rotundus) tubers were planted and treated preemergencewith the test chemicals dissolved in a non-phytotoxic solvent. At thesame time, these crop and weed species were treated with a soil/foliageapplication. At the time of treatment, the plants ranged in height from2 to 18 cm. Treated plants and controls were maintained in a greenhousefor sixteen days, after which all species were compared to controls andvisually rated for response to treatment. The ratings, summarized inTable A, are based on a numerical scale extending from 0=no injury, to10=complete kill. The accompanying descriptive symbols have thefollowing meanings:

B=burn;

C=chlorosis/necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effect;

U=unusual pigmentation;

X=axillary stimulation;

S=albinism; and

6Y=abscised buds or flowers.

                                      COMPOUNDS                                   __________________________________________________________________________     ##STR58##                                                                    Compound                                                                             R.sub.1     R.sub.2   X    Y    Z                                      __________________________________________________________________________    1     OCH.sub.3   CH.sub.2 CN                                                                              OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     2     OCH.sub.3   CH.sub.2 CN                                                                              OCH.sub.3                                                                          CH.sub.3                                                                           N                                      3     CO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     4     CO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH                                     5     CO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      6     CO.sub.2 CH.sub.3                                                                         CH.sub.2 P(O)(OCH.sub.3).sub.2                                                           OCH.sub.3                                                                          CH.sub.3                                                                           N                                      7     CO.sub.2 CH.sub.3                                                                         CH.sub.2 SCN                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     8     CO.sub.2 CH.sub.3                                                                         CH.sub.2 CN                                                                              OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     9     CO.sub.2 CH.sub. 3                                                                        CH.sub.2 CN                                                                              OCH.sub.3                                                                          CH.sub.3                                                                           N                                      10    OCH.sub.3   CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     11    OCH.sub.3   CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          CH.sub.3                                                                           CH                                     12    OCH.sub.3   CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                           CH.sub.3                                                                           CH                                     13    OCH.sub.3   CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          Cl   CH                                     14    OCH.sub.3   CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      15    OCH.sub.3   CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          CH.sub.3                                                                           N                                      16    OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     17    OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           CH                                     18    OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH                                     19    OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      20    OC.sub.2 H.sub.5                                                                          C(O)CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           N                                      21    COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     22    COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          CH.sub.3                                                                           CH                                     23    COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                           CH.sub.3                                                                           CH                                     24    COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         Cl   OCH.sub.3                                                                          CH                                     25    COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      26    COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          CH.sub.3                                                                           N                                      27    Cl          CH.sub.2 SCN                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          CH                                     28    Cl          CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     29    Cl          CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                                                          CH                                     30    Cl          CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                           CH.sub.3                                                                           CH                                     31    Cl          CH.sub.2 N.sub.3                                                                         Cl   OCH.sub.3                                                                          CH                                     32    Cl          CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      33    Cl          CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          CH.sub.3                                                                           N                                      34    SO.sub.2 CH.sub.3                                                                         C(O)H      OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     35    SO.sub.2 CH.sub.3                                                                         CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     36    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     37    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                                                          CH                                     38    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.3 N.sub.3                                                                         OCH.sub.3                                                                          CH.sub.3                                                                           N                                      39    COOCH.sub.3 CH.sub.2 CN                                                                              OCH.sub.3                                                                          CH.sub.3                                                                           CH                                     40    COOCH.sub.3 CH.sub.2 CN                                                                              CH.sub.3                                                                           CH.sub.3                                                                           CH                                     41    COOCH.sub.3 CH.sub.2 CN                                                                              Cl   OCH.sub.3                                                                          CH                                     42    COOCH.sub.3 CH.sub.2 CN                                                                              OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      43    COOCH.sub.2 CH.sub.3                                                                      C(O)H      OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     44    COOCH.sub.2 CH.sub.3                                                                      C(O)H      CH.sub.3                                                                           CH.sub.3                                                                           CH                                     45    COOCH.sub.2 CH.sub.3                                                                      C(O)H      Cl   OCH.sub.3                                                                          CH                                     46    COOCH.sub.2 CH.sub.3                                                                      C(O)H      OCH.sub.3                                                                          CH.sub.3                                                                           N                                      47    COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 CN                                                                              OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     48    COOCH(CH.sub.3).sub.2                                                                     CH.sub.2 CN                                                                              CH.sub.3                                                                           CH.sub.3                                                                           CH                                     49    COOCH.sub.3 C(O)H      OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     50    COOCH.sub.3 C(O)H      OCH.sub.3                                                                          CH.sub.3                                                                           CH                                     51    COOCH.sub.3 C(O)H      CH.sub.3                                                                           CH.sub.3                                                                           CH                                     52    COOCH.sub.3 C(O)H      Cl   OCH.sub.3                                                                          CH                                     53    COOCH.sub.3 C(O)H      OCH.sub.3                                                                          CH.sub.3                                                                           N                                      54    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     55    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          CH.sub.3                                                                           CH                                     56    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         CH.sub.3                                                                           CH.sub.3                                                                           CH                                     57    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         Cl   OCH.sub.3                                                                          CH                                     58    COOCH.sub.2 CH.sub. 2 CH.sub.3                                                            CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      59    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 N.sub.3                                                                         OCH.sub.3                                                                          CH.sub.3                                                                           N                                      60    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     61    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              OCH.sub.3                                                                          CH.sub.3                                                                           CH                                     62    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              CH.sub.3                                                                           CH.sub.3                                                                           CH                                     63    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              Cl   OCH.sub.3                                                                          CH                                     64    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      65    COOCH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.2 CN                                                                              OCH.sub.3                                                                          CH.sub.3                                                                           N                                      66    OCH.sub.2 CH.sub.2                                                                        C(CH.sub.3)NOH                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     67    OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOH                                                                           OCH.sub.3                                                                          CH.sub.3                                                                           CH                                     68    OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOH                                                                           Cl   OCH.sub.3                                                                          CH                                     69    OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOH                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      70    OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOH                                                                           OCH.sub.3                                                                          CH.sub.3                                                                           N                                      71    OCH.sub.2 CH.sub.3                                                                        C(CH.sub.3)NOCH.sub.3                                                                    OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     72    COOCH.sub.3 CHNOCH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                     73    COOCH.sub.3 CHNOCH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           CH                                     74    COOCH.sub.3 CHNOCH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH                                     75    COOCH.sub.3 CHNOCH.sub.3                                                                             Cl   OCH.sub.3                                                                          CH                                     76    COOCH.sub.3 CHNOCH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          N                                      77    COOCH.sub.3 CHNOCH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           N                                      __________________________________________________________________________

                  TABLE A                                                         ______________________________________                                                         Compound 1  Compound 2                                       Rate kg/ha       0.05        0.05                                             ______________________________________                                        POST-EMERGENCE                                                                Morningglory     10C         4C,8H                                            Cocklebur        9C          4C,9G                                            Velvetleaf       9C          2C,5G                                            Nutsedge         2C,8G       2C,5G                                            Crabgrass        2C,9G       2C,7G                                            Barnyardgrass    3C,9H       4C,9H                                            Cheatgrass       9G          6G                                               Wild Oats        3C,9G       3C,9G                                            Wheat            8G          9G                                               Corn             5C,9H       3C,9G                                            Soybean          5C,9G       4C,9G                                            Rice             5C,9G       6C,9G                                            Sorghum          4C,9H       5C,9H                                            Sugar beet       9C          9C                                               Cotton           9C          5C,9G                                            PRE-EMERGENCE                                                                 Morningglory     9G          9G                                               Cocklebur        8H          9H                                               Velvetleaf       9G          3G                                               Nutsedge         3C,8G       0                                                Crabgrass        0           0                                                Barnyardgrass    4C,9H       5G                                               Cheatgrass       8G          5G                                               Wild Oats        3C,8G       3C,8G                                            Wheat            3C,9G       3C,9H                                            Corn             3C,9G       2C,9H                                            Soybean          8H          3C,5H                                            Rice             3C,9H       5C,9H                                            Sorghum          10E         9H                                               Sugar beet       7G          4C,7G                                            Cotton           8G          6G                                               ______________________________________                                                         Compound 3  Compound 4                                       Rate kg/ha       0.05        0.05                                             ______________________________________                                        POST-EMERGENCE                                                                Morningglory     10C         3C,9G                                            Cocklebur        10C         2C,7G                                            Velvetleaf       10C         3C,7H                                            Nutsedge         4C,9G       5G                                               Crabgrass        3C,7G       3G                                               Barnyardgrass    6C,9H       4C,9H                                            Cheatgrass       6C,9G       5C,9G                                            Wild Oats        5C,9G       5C,9G                                            Wheat            7G          8G                                               Corn             4U,9C       5C,9G                                            Soybean          9C          4C,9G                                            Rice             5C,9G       5C,9G                                            Sorghum          9C          4C,9G                                            Sugar beet       9C          5C,8H                                            Cotton           9C          4C,7H                                            PRE-EMERGENCE                                                                 Morningglory     9G          8G                                               Cocklebur        9H          5G                                               Velvetleaf       9C          --                                               Nutsedge         4C,8G       0                                                Crabgrass        2C,8G       7G                                               Barnyardgrass    3C,8G       2H                                               Cheatgrass       4C,9H       2C,5G                                            Wild Oats        4C,8G       3C,6G                                            Wheat            6G          5G                                               Corn             3C,9G       4G                                               Soybean          3C,5H       3G                                               Rice             4C,8H       2C                                               Sorghum          4C,9H       3C,5G                                            Sugar beet       10C         4C,8H                                            Cotton           2C,8G       8G                                               ______________________________________                                                         Compound 5  Compound 6                                       Rate kg/ha       0.05        0.05                                             ______________________________________                                        POST-EMERGENCE                                                                Morningglory     2C,3H       2C,2G                                            Cocklebur        2G          2G                                               Velvetleaf       2H          2G                                               Nutsedge         0           0                                                Crabgrass        0           lH                                               Barnyardgrass    0           2H                                               Cheatgrass       0           0                                                Wild Oats        0           0                                                Wheat            0           0                                                Corn             0           2H                                               Soybean          1H          3H                                               Rice             2G          5G                                               Sorghum          0           5G                                               Sugar beet       1H          3H                                               Cotton           0           0                                                PRE-EMERGENCE                                                                 Morningglory     5G          2G                                               Cocklebur        0           0                                                Velvetleaf       0           0                                                Nutsedge         0           0                                                Crabgrass        4G          2G                                               Barnyardgrass    0           0                                                Cheatgrass       2G          0                                                Wild Oats        0           0                                                Wheat            0           2G                                               Corn             0           2G                                               Soybean          2G          4H                                               Rice             0           2G                                               Sorghum          0           0                                                Sugar beet       0           0                                                Cotton           --          --                                               ______________________________________                                                         Compound 7  Compound 8                                       Rate kg/ha       0.05        0.05                                             ______________________________________                                        POST-EMERGENCE                                                                Morningglory     10C         10C                                              Cocklebur        9C          10C                                              Velvetleaf       10C         10C                                              Nutsedge         9G          9C                                               Crabgrass        8G          4C,9G                                            Barnyardgrass    4C,9H       9C                                               Cheatgrass       4C,9G       9C                                               Wild Oats        6C,9G       9C                                               Wheat            4C,9G       9C                                               Corn             4U,9G       7U,9C                                            Soybean          5C,9G       9C                                               Rice             9C          9C                                               Sorghum          9C          9C                                               Sugar beet       9C          9C                                               Cotton           9C          9C                                               PRE-EMERGENCE                                                                 Morningglory     9G          9G                                               Cocklebur        10H         9H                                               Velvetleaf       9C          9G                                               Nutsedge         4C,9G       10E                                              Crabgrass        4C,8G       4C,9G                                            Barnyardgrass    4C,9G       4C,9H                                            Cheatgrass       4C,8H       4C,9G                                            Wild Oats        3C,8G       5C,9G                                            Wheat            5G          10E                                              Corn             8G          4C,9H                                            Soybean          2G          8H                                               Rice             9H          10E                                              Sorghum          2C,9G       10E                                              Sugar beet       10C         4C,9G                                            Cotton           9C          9G                                               ______________________________________                                                         Compound 9  Compound 10                                      Rate kg/ha       0.05        0.05                                             ______________________________________                                        POST-EMERGENCE                                                                Morningglory     10C         4G                                               Cocklebur        10C         7G                                               Velvetleaf       10C         4C,9G                                            Nutsedge         5C,9G       4C,9G                                            Crabgrass        2C,8G       2C,5G                                            Barnyardgrass    9C          3C,8H                                            Cheatgrass       6C,9G       2C,8G                                            Wild Oats        9C          3C,5G                                            Wheat            9C          6G                                               Corn             7U,9C       3C,9H                                            Soybean          9C          5C,9G                                            Rice             9C          2C,9G                                            Sorghum          9C          3C,9H                                            Sugar beet       9C          9C                                               Cotton           2C,9G       4C,9G                                            PRE-EMERGENCE                                                                 Morningglory     4C,9G       9G                                               Cocklebur        3C,9H       8G                                               Velvetleaf       4C,9G       8G                                               Nutsedge         10E         4G                                               Crabgrass        3C,7G       3G                                               Barnyardgrass    5C,9H       3C,8H                                            Cheatgrass       4C,8H       8H                                               Wild Oats        5C,9G       3C,8G                                            Wheat            5C,9G       7G                                               Corn             3C,9G       2C,7G                                            Soybean          2C,5H       3C,5H                                            Rice             10E         2C,8G                                            Sorghum          5C,9H       3C,9H                                            Sugar beet       10C         9C                                               Cotton           8G          9G                                               ______________________________________                                                         Compound 11 Compound 12                                      Rate kg/ha       0.05        0.05                                             ______________________________________                                        POST-EMERGENCE                                                                Morningglory     3C,8H       0                                                Cocklebur        7H          2H                                               Velvetleaf       3C,8H       3G                                               Nutsedge         2C,9G       0                                                Crabgrass        5G          0                                                Barnyardgrass    3C,9H       0                                                Cheatgrass       9G          0                                                Wild Oats        3C,5G       0                                                Wheat            9G          0                                                Corn             9G          2C,7H                                            Soybean          4C,9G       3C,8G                                            Rice             5C,9G       6G                                               Sorghum          9H          6G                                               Sugar beet       3C,8G       2H                                               Cotton           3C,9G       2C,2G                                            PRE-EMERGENCE                                                                 Morningglory     8G          0                                                Cocklebur        8H          8H                                               Velvetleaf       4C,9G       3G                                               Nutsedge         5G          0                                                Crabgrass        4G          0                                                Barnyardgrass    9H          0                                                Cheatgrass       3C,9H       0                                                Wild Oats        3C,9G       0                                                Wheat            9G          0                                                Corn             2C,9G       0                                                Soybean          4C,8H       2C,2H                                            Rice             8H          0                                                Sorghum          10E         0                                                Sugar beet       4C,9G       8G                                               Cotton           9G          3G                                               ______________________________________                                                         Compound 13 Compound 14                                      Rate kg/ha       0.05        0.05                                             ______________________________________                                        POST-EMERGENCE                                                                Morningglory     2C,4G       3C,9G                                            Cocklebur        5G          5C,9G                                            Velvetleaf       0           2C,6H                                            Nutsedge         2C,4G       0                                                Crabgrass        0           2G                                               Barnyardgrass    0           2C,3H                                            Cheatgrass       0           0                                                Wild Oats        0           2G                                               Wheat            0           3G                                               Corn             0           3C,8H                                            Soybean          3H          5C,9G                                            Rice             5G          2C,8G                                            Sorghum          2C,5G       3C,8H                                            Sugar beet       3C,5G       4C,9G                                            Cotton           3C,7G       2C,5G                                            PRE-EMERGENCE                                                                 Morningglory     8G          7H                                               Cocklebur        --          9H                                               Velvetleaf       5G          4G                                               Nutsedge         5G          0                                                Crabgrass        2G          0                                                Barnyardgrass    0           1C                                               Cheatgrass       0           2G                                               Wild Oats        0           2C,4G                                            Wheat            0           6G                                               Corn             5G          2C,6G                                            Soybean          2C,2G       6H                                               Rice             2C          8G                                               Sorghum          2C,4G       2C,7H                                            Sugar beet       6G          10C                                              Cotton           6G          2G                                               ______________________________________                                                       Compound 15                                                                             Compound 16                                          Rate kg/ha       0.05    0.4     0.05                                         ______________________________________                                        POST-EMERGENCE                                                                Morningglory     4C,8H   10C     1C,1H                                        Cocklebur        9H      10C     3C,9H                                        Velvetleaf       4C,8H   9C      5C,9G                                        Nutsedge         0       5C,9G   4C,9G                                        Crabgrass        4G      4C,9G   3G                                           Barnyardgrass    4C,8H   6C,9H   3C,9H                                        Cheatgrass       2C,5G   2C,8G   2G                                           Wild Oats        3C,9G   3C,9G   4G                                           Wheat            6G      5C,9G   5G                                           Corn             4C,9H   4C,9G   2C,9H                                        Soybean          5C,9G   5C,9G   2C,7G                                        Rice             5C,9G   5C,9G   4C,9G                                        Sorghum          3C,9H   3C,9H   5C,9G                                        Sugar beet       9C      9C      3C,6G                                        Cotton           4C,8G   9C      5C,9G                                        PRE-EMERGENCE                                                                 Morningglory     7G      9G      8G                                           Cocklebur        7H      8H      9H                                           Velvetleaf       5H      5C,9G   9G                                           Nutsedge         4G      7G      2C,7G                                        Crabgrass        0       5G      0                                            Barnyardgrass    2C,5G   3C,9H   3C,9H                                        Cheatgrass       6G      3C,8H   3C,6G                                        Wild Oats        2C,8G   5C,9G   3C,8G                                        Wheat            2C,9G   9C      7G                                           Corn             3C,9G   9G      9G                                           Soybean          3C,6H   9H      3C,4G                                        Rice             2C,8H   10E     4C,8H                                        Sorghum          3C,9H   5C,9H   4C,9H                                        Sugar beet       4C,9G   9C      4C,8G                                        Cotton           7G      9G      7G                                           ______________________________________                                                         Compound 17 Compound 18                                      Rate kg/ha       0.05        0.05                                             ______________________________________                                        POST-EMERGENCE                                                                Morningglory     3G          1H                                               Cocklebur        5C,9H       6G                                               Velvetleaf       4C,9G       6H                                               Nutsedge         3C,6G       0                                                Crabgrass        3C,4G       0                                                Barnyardgrass    3C,9H       1C,2H                                            Cheatgrass       4G          0                                                Wild Oats        0           0                                                Wheat            2G          0                                                Corn             3C,9H       3C,7H                                            Soybean          3C,7G       2H                                               Rice             2C,8G       5G                                               Sorghum          4C,9H       2C,5G                                            Sugar beet       4G          2G                                               Cotton           9C          4G                                               PRE-EMERGENCE                                                                 Morningglory     9G          2H                                               Cocklebur        8H          7H                                               Velvetleaf       4C,9G       4G                                               Nutsedge         5G          0                                                Crabgrass        4G          0                                                Barnyardgrass    3C,9H       2C                                               Cheatgrass       3C,7G       0                                                Wild Oats        3C,8G       0                                                Wheat            3C,9G       0                                                Corn             3C,9H       3C,6G                                            Soybean          3C,7H       1C                                               Rice             4C,8H       2C,5G                                            Sorghum          3C,9H       5G                                               Sugar beet       4C,9G       9G                                               Cotton           8G          5G                                               ______________________________________                                                         Compound 19 Compound 20                                      Rate kg/ha       0.05        0.05                                             ______________________________________                                        POST-EMERGENCE                                                                Morningglory     3G          0                                                Cocklebur        4C,9G       4C,9G                                            Velvetleaf       2C,7G       2C,5G                                            Nutsedge         0           5G                                               Crabgrass        4G          4G                                               Barnyardgrass    3C,7H       3C,8H                                            Cheatgrass       0           0                                                Wild Oats        0           0                                                Wheat            0           0                                                Corn             3C,9H       4C,9G                                            Soybean          2C,5H       3H,5G                                            Rice             2C,9G       5C,9G                                            Sorghum          3C,8G       4C,9H                                            Sugar beet       3C,4H       3C,6H                                            Cotton           3C,5G       3C,5G                                            PRE-EMERGENCE                                                                 Morningglory     8G          6G                                               Cocklebur        8H          8G                                               Velvetleaf       7G          5G                                               Nutsedge         0           0                                                Crabgrass        0           0                                                Barnyardgrass    5H          3C,7G                                            Cheatgrass       0           0                                                Wild Oats        0           0                                                Wheat            0           0                                                Corn             3C,9H       9G                                               Soybean          2C,4G       2C,6G                                            Rice             3C,9H       9H                                               Sorghum          3C,8H       3C,9H                                            Sugar beet       3C,7G       4C,8G                                            Cotton           7G          7G                                               ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   21      22      23    24                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     10C     10C     9C    9C                                     Cocklebur        10C     9C      10C   9C                                     Velvetleaf       10C     9C      9C    5C,9G                                  Nutsedge         5C,9G   4C,9G   4C,9G 2C,8G                                  Crabgrass        0       0       2G    0                                      Giant Foxtail    3C,6G   3C,6G   4C,9G 1H                                     Barnyardgrass    10C     4C,9H   9C    3C,8H                                  Cheatgrass       5C,9G   3C,9G   9G    2G                                     Wild Oats        2C,5G   0       10C   0                                      Wheat            4C,9G   7G      2C,9G 0                                      Corn             9C      4C,9H   9C    2C,5G                                  Barley           8G      9G      9C    2G                                     Soybean          9C      4C,9G   3C,9G 3H,4G                                  Rice             9C      4C,9G   9C    4C,9G                                  Sorghum          9C      2C,9H   9C    9H                                     Sugar beet       9C      9C      9C    5C,9G                                  Cotton           9C      5C,9G   10C   10C                                    PREEMERGENCE                                                                  Morningglory     9G      9H      7H    9G                                     Cocklebur        9H      9H      9H    9H                                     Velvetleaf       10C     9C      8G    8G                                     Nutsedge         9G      8G      9G    0                                      Crabgrass        0       2G      2G    0                                      Giant Foxtail    3C,7G   3C,6G   4C,8G 2C,2G                                  Barnyardgrass    4C,9H   4C,9H   4C,8H 2C,5G                                  Cheatgrass       3C,9H   9G      9G    4G                                     Wild Oats        7G      3C,7G   7G    0                                      Wheat            9H      9G      8G    0                                      Corn             3C,9H   9H      5C,9H 7G                                     Barley           9G      9G      9G    7G                                     Soybean          2C,7H   3C,8H   4C,6H 0                                      Rice             4C,9H   2C,8G   4C,9H 3C,7G                                  Sorghum          4C,9H   9H      5C,9H 4C,8H                                  Sugar beet       5C,9G   9G      4C,9G 9G                                     Cotton           8G      9G      9G    8G                                     ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   25      26      27    28                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     9C      10C     3C,7H 10C                                    Cocklebur        10C     10C     0     8H                                     Velvetleaf       5C,9G   10C     0     10C                                    Nutsedge         5C,9G   5C,9G   0     6C,9G                                  Crabgrass        2G      0       0     0                                      Giant Foxtail    3C,9G   4C,9G   0     3C,7G                                  Barnyardgrass    3C,8H   4C,9H   5H    4C,9H                                  Cheatgrass       7G      2C,9G   0     7G                                     Wild Oats        3G      9C      0     0                                      Wheat            4G      4G      0     0                                      Corn             9C      10C     5H    3C,8H                                  Barley           4G      7G      0     2C                                     Soybean          5C,9G   10C     3H    4C,9G                                  Rice             9C      9C      0     3C,9G                                  Sorghum          3C,9H   9C      3G    7G                                     Sugar beet       5C,9G   10C     4C,6G 10C                                    Cotton           10C     10C     0     4C,9G                                  PREEMERGENCE                                                                  Morningglory     8G      9G      5G    7G                                     Cocklebur        --      --      8G    9H                                     Velvetleaf       6G      4C,9G   8G    9G                                     Nutsedge         8G      10E     0     3G                                     Crabgrass        4G      3G      0     5G                                     Giant Foxtail    2C,5G   3C,5G   0     4C,6G                                  Barnyardgrass    3C,6G   3C,8H   0     4C,7H                                  Cheatgrass       6G      9H      0     5G                                     Wild Oats        2G      2C,8G   0     2G                                     Wheat            4G      3C,9H   0     0                                      Corn             3C,9G   3C,9G   2C,3G 7G                                     Barley           8G      9G      2G    7G                                     Soybean          2C,6G   3C,7H   0     2C,5H                                  Rice             8G      9H      4G    2C,6H                                  Sorghum          3C,8H   3C,9H   0     2C,4H                                  Sugar beet       5C,9G   5C,9G   8G    10C                                    Cotton           8G      9G      3G    7G                                     ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   29      30      31    32                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     9C      0       3G    10C                                    Cocklebur        9H      4C,9H   4C,9H 10C                                    Velvetleaf       10C     8G      0     2C,5G                                  Nutsedge         4C,8G   0       0     5G                                     Crabgrass        0       0       0     0                                      Giant Foxtail    4G      0       0     2C,4G                                  Barnyardgrass    3C,8H   0       4H    3C,9H                                  Cheatgrass       2C,5G   0       0     0                                      Wild Oats        2C      0       0     2C,5G                                  Wheat            0       0       0     0                                      Corn             9H      0       0     3C,9H                                  Barley           5G      0       0     2G                                     Soybean          3H,9G   7G      2G    4C,9G                                  Rice             8G      5G      0     4C,9G                                  Sorghum          3C,9H   3C,7H   2G    2C,7G                                  Sugar beet       10C     6C,9G   2G    10C                                    Cotton           4C,9G   5G      4C,8G 9C                                     PREEMERGENCE                                                                  Morningglory     7G      5G      7G    8G                                     Cocklebur        8H      9H      9H    9H                                     Velvetleaf       9G      9G      9G    9C                                     Nutsedge         10E     5G      10E   0                                      Crabgrass        3G      0       0     0                                      Giant Foxtail    4C,7G   5G      4G    8G                                     Barnyardgrass    4C,8H   2G      2G    3C,7G                                  Cheatgrass       3C,7G   0       0     4G                                     Wild Oats        5G      4G      0     5G                                     Wheat            5G      0       0     0                                      Corn             3C,8H   3G      2C,6G 2C,7G                                  Barley           9G      3G      0     2C,8G                                  Soybean          3C,8H   1C      0     3C,5H                                  Rice             4C,9H   3G      3G    9H                                     Sorghum          3C,5G   5G      5G    5G                                     Sugar beet       9C      8G      9G    10C                                    Cotton           7G      7G      8G    7G                                     ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   33      34      35    36                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     10C     10C     10C   10C                                    Cocklebur        9C      10C     10C   9C                                     Velvetleaf       4C,8G   10C     10C   9C                                     Nutsedge         2C,5G   5C,9G   10C   4C,9G                                  Crabgrass        2G      8G      9C    0                                      Giant Foxtail    6G      5C,9G   9C    4G                                     Barnyardgrass    4C,9H   9C      9C    4C,9H                                  Cheatgrass       5G      4C,9G   9C    8G                                     Wild Oats        3G      4C,8G   4C,9G 0                                      Wheat            3G      9G      9G    3G                                     Corn             3C,9H   5C,9G   6C,9G 2H                                     Barley           0       9C      5C,9G 9G                                     Soybean          4C,9G   6C,9G   5C,9G 3C,9G                                  Rice             5C,9G   9C      9C    5C,9G                                  Sorghum          4C,9H   9C      9C    4C,9H                                  Sugar beet       9C      9C      10C   9C                                     Cotton           4C,9G   10C     10C   4C,9G                                  PREEMERGENCE                                                                  Morningglory     7G      10C     8G    1H                                     Cocklebur        --      9H      8H    3H                                     Velvetleaf       6G      9G      8G    5G                                     Nutsedge         10E     8G      9G    3G                                     Crabgrass        0       0       3G    0                                      Giant Foxtail    0       4C,9H   3C,8G 2G                                     Barnyardgrass    2C,7G   4C,9H   3C,9H 7G                                     Cheatgrass       0       9H      9H    3G                                     Wild Oats        2G      2C,8G   3C,8G 0                                      Wheat            0       6C,9H   10H   0                                      Corn             2C,5G   9H      5C,9H 3C,7G                                  Barley           2G      9G      9G    9G                                     Soybean          3C,3H   7H      3C,7G 2H                                     Rice             7G      10E     10E   8H                                     Sorghum          3C,3H   5C,9H   10H   3C,7G                                  Sugar beet       8G      9G      8G    7H                                     Cotton           6G      9G      9G    2G                                     ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   37      38      39    40                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     5C,9G   3C,8G   10C   10C                                    Cocklebur        4C,9H   4C,9G   10C   10C                                    Velvetleaf       5C,9G   4C,9H   10C   10C                                    Nutsedge         5G      2G      9C    10C                                    Crabgrass        0       0       9C    5C,9G                                  Giant Foxtail    2G      2G      10C   9C                                     Barnyardgrass    3C,8H   2C,5H   9C    9C                                     Cheatgrass       8G      0       9C    9C                                     Wild Oats        2G      0       9C    9C                                     Wheat            3G      0       9C    2C,9G                                  Corn             0       3C,9H   9C    5C,9G                                  Barley           4C,9G   0       9C    9C                                     Soybean          4C,9G   2C,7H   9C    9C                                     Rice             4C,8G   3C,8G   9C    9C                                     Sorghum          2C,7G   3C,8H   9C    9C                                     Sugar beet       3C,7H   5C,9G   9C    9C                                     Cotton           4C,9H   4C,8H   10C   10C                                    PREEMERGENCE                                                                  Morningglory     3G      7H      10E   9H                                     Cocklebur        9H      7H      9H    9C                                     Velvetleaf       7H      7G      10E   9C                                     Nutsedge         0       0       10E   10C                                    Crabgrass        0       0       5C,9G 5C,9G                                  Giant Foxtail    3G      1C      9C    5C,9H                                  Barnyardgrass    7H      2C      5C,9H 5C,9H                                  Cheatgrass       6G      0       10E   10E                                    Wild Oats        2G      0       6C,9H 5C,9H                                  Wheat            3G      0       10E   10E                                    Corn             2C,6G   6G      10E   5C,9H                                  Barley           3C,9G   3G      4C,9G 5C,9H                                  Soybean          2C,5G   2C      9H    9H                                     Rice             3C,7H   2C,5G   10H   10E                                    Sorghum          4C,9H   2C,5G   10H   10E                                    Sugar beet       5H      5G      9C    5C,9G                                  Cotton           0       6G      9C    10C                                    ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   41      42      43    44                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     10C     10C     10C   5C,9H                                  Cocklebur        10C     10C     10C   2C,8H                                  Velvetleaf       9C      6G      3C,8G 2H,5G                                  Nutsedge         9C      9C      2C,8G 2C,8G                                  Crabgrass        4C,8G   3C,7G   2G    0                                      Giant Foxtail    9C      3C,8G   1C,6G 0                                      Barnyardgrass    9C      9C      9C    4C,9H                                  Cheatgrass       4C,9G   2C,9G   1C,5G 3G                                     Wild Oats        5C,9G   9G      0     0                                      Wheat            9C      2C,9G   0     0                                      Corn             5C,9G   10C     4C,9G 3C,9G                                  Barley           4C,9G   9C      6G    2C,9G                                  Soybean          9C      9C      2C,8H 2C,7H                                  Rice             9C      9C      4C,9G 3C,9G                                  Sorghum          9C      3C,9G   3C,9G 3C,9G                                  Sugar beet       9C      9C      2C,4G 2C,6G                                  Cotton           10C     9C      9C    3C,8G                                  PREEMERGENCE                                                                  Morningglory     9G      9G      7G    4G                                     Cocklebur        9H      8H      9H    2C,7G                                  Velvetleaf       10C     8G      2C,4G 4G                                     Nutsedge         10E     10E     9G    7G                                     Crabgrass        3G      2C,5G   9G    2C,8G                                  Giant Foxtail    3C,9H   3C,8G   2C,4G 2C,5G                                  Barnyardgrass    3C,9H   8H      9H    2C,7H                                  Cheatgrass       8G      7G      4G    2G                                     Wild Oats        6C,9H   4C,9G   5G    2G                                     Wheat            4C,9H   4C,9H   4G    0                                      Corn             9H      4C,9H   2C,9H 5C,9H                                  Barley           3C,9H   4C,9H   7G    6G                                     Soybean          9H      4C,8H   2C,7H 2C,5H                                  Rice             10E     10E     4C,9H 5C,9H                                  Sorghum          10H     5C,9H   2C,9H 3C,9H                                  Sugar beet       5C,9G   4C,9G   2C,4G 2C,4G                                  Cotton           9G      9G      9G    2C,6G                                  ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   45      46      47    48                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     5C,9G   5C,8H   10C   10C                                    Cocklebur        2C,6G   4C,9H   10C   10C                                    Velvetleaf       0       2G      5C,9G 3C,8G                                  Nutsedge         0       0       4C,9G 2C,9G                                  Crabgrass        2G      1C,3G   2C,4G 7G                                     Giant Foxtail    0       2C,5G   5C,9H 4C,9G                                  Barnyardgrass    8H      9C      9C    9C                                     Cheatgrass       2G      2C      2C,5G 4C,9G                                  Wild Oats        0       0       2C,6G 3C,9G                                  Wheat            0       0       6G    4C,9G                                  Corn             2C,4H   9G      4U,9G 4U,9G                                  Barley           0       0       3C,8H 4C,9G                                  Soybean          lC,lH   2H      9C    9C                                     Rice             2G      5C,9G   5C,9G 6C,9G                                  Sorghum          8G      2C,8H   9C    6C,9G                                  Sugar beet       0       3C,7H   10C   9C                                     Cotton           3C,8G   2C,6G   10C   9C                                     PREEMERGENCE                                                                  Morningglory     2C,5G   0       9G    8G                                     Cocklebur        2C,5H   0       9H    8H                                     Velvetleaf       0       0       3C,7G 8G                                     Nutsedge         3C,8G   0       5G    3C,9G                                  Crabgrass        0       0       0     3G                                     Giant Foxtail    0       0       3C,7G 8G                                     Barnyardgrass    3C,8H   2C,8H   9H    3C,9H                                  Cheatgrass       0       0       8G    8G                                     Wild Oats        0       0       6G    8G                                     Wheat            0       0       7G    9H                                     Corn             2C,8H   0       3C,9G 3C,9G                                  Barley           7G      0       7G    9G                                     Soybean          0       0       7H    3C,7H                                  Rice             2C,8H   0       3C,9H 9H                                     Sorghum          2C,9H   0       9H    9H                                     Sugar beet       0       0       3C,9G 9G                                     Cotton           1C,3G   0       8G    9G                                     ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   49      50      51    52                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     10C     9C      9C    6G                                     Cocklebur        9C      4C,9G   9C    4C,9H                                  Velvetleaf       10H     3C,6G   3C,5H 2H                                     Nutsedge         4G      4G      5G    4G                                     Crabgrass        2C,7G   4G      4G    3G                                     Giant Foxtail    9C      3C,7H   4C,9G 6G                                     Barnyardgrass    9C      9C      9C    9C                                     Cheatgrass       6G      4G      5G    0                                      Wild Oats        2C,4G   0       0     0                                      Wheat            3G      3G      2G    0                                      Corn             4C,9H   2C,8G   3C,9G 2C,9H                                  Barley           4C,9G   3C,7G   2C,7G 6G                                     Soybean          9C      5C,9G   5C,9G 3C,7H                                  Rice             9C      9C      9C    9C                                     Sorghum          9C      3C,8G   9H    4C,9G                                  Sugar beet       10C     5C,9G   2C,6G 3C,5H                                  Cotton           10C     10C     10C   10C                                    PREEMERGENCE                                                                  Morningglory     8H      1H      7H    0                                      Cocklebur        9H      0       2C,2H 1H                                     Velvetleaf       4G      2G      2G    0                                      Nutsedge         7G      0       4G    8G                                     Crabgrass        --      5G      8G    8G                                     Giant Foxtail    6G      3G      4G    0                                      Barnyardgrass    9H      3C,9H   4G    9H                                     Cheatgrass       2C,7G   7G      0     0                                      Wild Oats        8G      4G      6G    4G                                     Wheat            5G      6G      7G    4G                                     Corn             3C,9G   2C,7G   2C,6G 2C,3G                                  Barley           2C,9G   2G      4G    2C,5G                                  Soybean          3C,9H   3C,8H   3C,8H 2C,3H                                  Rice             5C,9H   9H      9H    5C,9H                                  Sorghum          9H      9H      9H    9H                                     Sugar beet       9G      4H      7G    3G                                     Cotton           9G      8G      3C,9G 8G                                     ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   53      54      55    56                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     3C,8H   10C     10C   6C,9G                                  Cocklebur        3C,8H   10C     9H    2C,9H                                  Velvetleaf       2C,3H   10C     9C    10C                                    Nutsedge         0       3C,9G   2C,9G 2C,7G                                  Crabgrass        8G      0       3G    3G                                     Giant Foxtail    3C,9G   5G      2C,9G 7G                                     Barnyardgrass    5C,9H   4C,9G   4C,8G 1C,7G                                  Cheatgrass       7G      3C,9G   3C,9G 8G                                     Wild Oats        0       3G      2C,5G 2C,6G                                  Wheat            3G      8G      9G    7G                                     Corn             2C,9H   9G      2C,9G 3C,9H                                  Barley           2C,5G   9G      8G    8G                                     Soybean          8G      3C,9G   3C,9H 2C,8G                                  Rice             9C      2C,9G   9G    2C,9G                                  Sorghum          4C,9G   9G      2C,9G 2C,9G                                  Sugar beet       8G      9C      9C    9C                                     Cotton           3C,5G   9C      9C    10C                                    PREEMERGENCE                                                                  Morningglory     0       0       7G    3H                                     Cocklebur        0       3H      --    2C,3H                                  Velvetleaf       0       1C,5G   4C,7G 2C,7G                                  Nutsedge         0       7G      3C,9G 7G                                     Crabgrass        0       2G      0     0                                      Giant Foxtail    0       2G      7G    2G                                     Barnyardgrass    0       3C,7H   2C,9H 2C,9H                                  Cheatgrass       0       5G      7H    7H                                     Wild Oats        0       2G      2C,3G 2C,5G                                  Wheat            0       0       7G    5G                                     Corn             0       2G      6G    1C,6G                                  Barley           0       5G      8G    4G                                     Soybean          0       3C      3C,7H 2C,7H                                  Rice             5G      3C,7H   3C,7G 3C,8H                                  Sorghum          4G      2C,7H   2C,9H 3C,9H                                  Sugar beet       0       4C,8G   4C    3C                                     Cotton           0       0       2C,4G 3G                                     ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   57      58      59    60                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     10C     2C,7G   10C   10C                                    Cocklebur        10C     10C     10C   10C                                    Velvetleaf       9C      9C      9C    10C                                    Nutsedge         4C,9G   9G      9G    4C,9G                                  Crabgrass        0       3G      5G    4G                                     Giant Foxtail    5G      5G      7G    3C,6G                                  Barnyardgrass    2C,6G   2C,6H   5C,9H 5C,9H                                  Cheatgrass       6G      2C,6G   2C,7G 9G                                     Wild Oats        1C      0       0     3C,5G                                  Wheat            2G      0       2G    6G                                     Corn             5G      3C,7G   3C,7H 2U,9G                                  Barley           4G      3G      5G    9G                                     Soybean          0       4C,9G   5C,9G 9C                                     Rice             5G      7G      9G    4C,9G                                  Sorghum          3C,9G   3C,8H   3C,9G 4C,9G                                  Sugar beet       5C,9G   4C,9G   9C    9C                                     Cotton           10C     10C     9C    10C                                    PREEMERGENCE                                                                  Morningglory     3G      6H      6G    5G                                     Cocklebur        8H      2C,2H   5H    7H                                     Velvetleaf       5G      6G      7G    7G                                     Nutsedge         0       10E     7G    5G                                     Crabgrass        2G      3G      5G    2G                                     Giant Foxtail    2G      5G      6G    0                                      Barnyardgrass    7G      5G      3C,8H 9H                                     Cheatgrass       3G      3G      5G    8G                                     Wild Oats        0       2G      2G    2G                                     Wheat            0       2G      3G    7G                                     Corn             2G      3G      2C,6G 3C,8H                                  Barley           0       5G      5G    2C,8G                                  Soybean          0       2C,5G   3C,4H 7H                                     Rice             5G      4C,8H   5C,9H 8H                                     Sorghum          3C,6G   3C,5G   4C,8G 3C,9H                                  Sugar beet       8G      9G      9G    6H                                     Cotton           0       3G      2G    0                                      ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   61      62      63    64                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     10C     10C     10C   10C                                    Cocklebur        10C     10C     10C   10C                                    Velvetleaf       10C     9C      3C,8G 3C,9G                                  Nutsedge         4C,9G   3C,9G   3G    2C,8G                                  Crabgrass        3G      5G      2G    0                                      Giant Foxtail    3C,8G   3C,8G   4G    4G                                     Barnyardgrass    9C      9C      4C,9H 3C,8G                                  Cheatgrass       4C,9G   3C,9G   2C,4G 2C,5G                                  Wild Oats        2C,7G   5C,9G   2G    2C,7G                                  Wheat            3C,9G   3C,9G   4G    2G                                     Corn             9C      2U,9G   3C,7H 2C,7G                                  Barley           9H      9H      3C,6G 4G                                     Soybean          9C      9C      3C,3H 4C,9G                                  Rice             5C,9G   5C,9G   9G    2C,8G                                  Sorghum          5C,9G   4C,9G   4C,9G 3C,9H                                  Sugar beet       9C      9C      4C,8H 9C                                     Cotton           10C     10C     4C,9G 3C,8G                                  PREEMERGENCE                                                                  Morningglory     4C,8G   5H      8G    2C,8G                                  Cocklebur        7H      6H      2C,4H 3C,7H                                  Velvetleaf       7H      3C,8H   7G    5G                                     Nutsedge         8G      8G      5G    8G                                     Crabgrass        3G      0       0     0                                      Giant Foxtail    6G      5G      4G    0                                      Barnyard grass   9H      7G      8H    7H                                     Cheatgrass       5C,9G   8G      5G    2G                                     Wild Oats        4C,8G   3C,8H   2G    2C,3G                                  Wheat            4C,9H   9G      3G    0                                      Corn             3C,9H   3C,9H   3C,4G 2C,5G                                  Barley           9G      8G      0     0                                      Soybean          4C,7H   7G      0     3C,7H                                  Rice             5C,9H   9H      7H    9H                                     Sorghum          9H      9H      9H    3C,8H                                  Sugar beet       9C      3C,7G   8G    3C,8G                                  Cotton           3C,8H   2C,7G   9G    2C,5G                                  ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   65      66      67    68                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     10C     2C,5G   2C,6G 2H                                     Cocklebur        10C     3C,9H   3C,9H 3H                                     Velvetleaf       9C      2C,9G   2C,5H 1H                                     Nutsedge         2C,8G   3C,9G   2C,5G 4G                                     Crabgrass        0       5G      0     0                                      Giant Foxtail    2C,7G   2C,6G   2C,6G 2G                                     Barnyardgrass    3C,9G   3C,9H   9H    7H                                     Cheatgrass       8G      4G      6G    0                                      Wild Oats        2C,9G   5G      2C,7G 0                                      Wheat            3G      2G      5G    0                                      Corn             3C,9H   3C,9H   2C,9H 0                                      Barley           2C,6G   8G      7G    0                                      Soybean          5C,9G   5H      3C,7H 1H                                     Rice             5C,9G   2C,7G   3C,7G 2G                                     Sorghum          9G      3C,6G   3C,8H 5G                                     Sugar beet       9C      2C,7G   3C,8H 3G                                     Cotton           9C      7G      3C,8G 0                                      PREEMERGENCE                                                                  Morningglory     2C,8G   0       0     0                                      Cocklebur        6H      2H      0     --                                     Velvetleaf       4G      0       0     0                                      Nutsedge         2C,8G   0       0     0                                      Crabgrass        0       0       5G    0                                      Giant Foxtail    0       0       5G    0                                      Barnyardgrass    7H      0       7G    9H                                     Cheatgrass       6H      0       2G    0                                      Wild Oats        3C,8G   0       2G    0                                      Wheat            0       0       2G    0                                      Corn             3C,6G   2G      2C,7G 2G                                     Barley           2G      0       7G    4G                                     Soybean          4C,8H   0       1H    0                                      Rice             10H     4G      3G    4G                                     Sorghum          9H      5G      3C,7G 4G                                     Sugar beet       3C,9G   3G      8G    0                                      Cotton           2C,8G   0       2G    0                                      ______________________________________                                                         Cmpd.   Cmpd.   Cmpd. Cmpd.                                                   69      70      71    72                                     Rate kg/ha       0.05    0.05    0.05  0.05                                   ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     1H      2C,4G   4C,9H 10C                                    Cocklebur        2C,7H   5H      3C,9H 10C                                    Velvetleaf       5H      2C,5G   9C    10C                                    Nutsedge         0       0       2C,8G 5C,9G                                  Crabgrass        0       0       5G    7G                                     Giant Foxtail    2G      2G      6G    9C                                     Barnyardgrass    0       6H      2C,7G 9C                                     Cheatgrass       2G      0       0     9C                                     Wild Oats        2G      2C,3G   2C,8G 3C,8G                                  Wheat            4G      0       6G    2C,9G                                  Corn             2C,5G   3C,9H   3C,9H 4U,9G                                  Barley           3G      0       3C,8G 3C,9G                                  Soybean          3C,7H   2C,3H   4C,9H 9C                                     Rice             3C,9G   8G      2C,6G 9C                                     Sorghum          3C,9H   3C,9H   2C,9H 9C                                     Sugar beet       3C,6G   3C,7H   2C,6G 10C                                    Cotton           4G      2C      2C,8G 10C                                    PREEMERGENCE                                                                  Morningglory     3G      0       2G    9G                                     Cocklebur        --      0       5H    6H                                     Velvetleaf       3G      0       0     2C,8G                                  Nutsedge         0       3G      0     9G                                     Crabgrass        0       3G      7H    0                                      Giant Foxtail    10H     --      5H    5G                                     Barnyardgrass    0       3G      2C,6H 8H                                     Cheatgrass       0       3G      2C,6H 8G                                     Wild Oats        0       4G      0     8G                                     Wheat            0       0       2G    8G                                     Corn             0       3G      2C,6H 9G                                     Barley           3G      4G      0     8G                                     Soybean          0       0       0     7H                                     Rice             0       5G      3C,7G 3C,9H                                  Sorghum          0       6G      2C,9H 9G                                     Sugar beet       2G      5G      6G    7G                                     Cotton           4G      5G      0     7G                                     ______________________________________                                                         Cmpd. 73 Cmpd. 74 Cmpd. 75                                   Rate kg/ha       0.05     0.05     0.05                                       ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     10C      9C       10C                                        Cocklebur        10C      10C      10C                                        Velvetleaf       10C      10C      10C                                        Nutsedge         9C       9C       6C,9G                                      Crabgrass        0        3C,8H    0                                          Giant Foxtail    6C,9G    6C,9H    5C,9G                                      Barnyardgrass    9C       9C       9C                                         Cheatgrass       9C       9C       3C,9G                                      Wild Oats        5C,9G    9C       2C,5G                                      Wheat            9G       9G       3G                                         Corn             2U,9G    9G       3C,9H                                      Barley           4C,9G    4C,9G    4C,9H                                      Soybean          9C       9C       5C,9G                                      Rice             9C       9C       5C,9G                                      Sorghum          5C,9G    9C       9C                                         Sugar beet       10C      10C      9C                                         Cotton           10C      9C       10C                                        PREEMERGENCE                                                                  Morningglory     9G       9G       8G                                         Cocklebur        --       9H       3C,5H                                      Velvetleaf       9C       5C,9G    5H                                         Nutsedge         10E      10E      9G                                         Crabgrass        3G       2G       0                                          Giant Foxtail    3C,9H    7G       3C,6G                                      Barnyardgrass    9H       9H       9H                                         Cheatgrass       9H       9H       9H                                         Wild Oats        3C,9G    2C,9H    3C,6G                                      Wheat            3C,9G    3C,9H    5G                                         Corn             3C,9H    3C,9G    3C,9H                                      Barley           9G       9G       7G                                         Soybean          9H       9H       7H                                         Rice             9H       10E      9H                                         Sorghum          9H       10E      3C,9H                                      Sugar beet       4C,9G    9G       8G                                         Cotton           9G       9G       9G                                         ______________________________________                                                          Cmpd. 76   Cmpd. 77                                         Rate kg/ha        0.05       0.05                                             ______________________________________                                        POSTEMERGENCE                                                                 Morningglory      10C        10C                                              Cocklebur         10C        10C                                              Velvetleaf        10C        10C                                              Nutsedge          2C,8G      9G                                               Crabgrass         3G         6G                                               Giant Foxtail     4C,9G      4C,9G                                            Barnyardgrass     9H         9C                                               Cheatgrass        9C         5C,9G                                            Wild Oats         9C         9C                                               Wheat             4C,9G      4C,9G                                            Corn              2C,8H      3U,9G                                            Barley            4C,9G      3C,9G                                            Soybean           9C         9C                                               Rice              9C         9C                                               Sorghum           4C,9G      5C,9G                                            Sugar beet        10C        9C                                               Cotton            4C,9G      10C                                              PREEMERGENCE                                                                  Morningglory      9G         9G                                               Cocklebur         9H         9H                                               Velvetleaf        4C,8H      4C,8H                                            Nutsedge          5G         4G                                               Crabgrass         0          0                                                Giant Foxtail     5G         5G                                               Barnyardgrass     8H         8H                                               Cheatgrass        9H         9H                                               Wild Oats         3C,9G      4C,9G                                            Wheat             9H         4C,9H                                            Corn              7G         2C,9G                                            Barley            9G         9G                                               Soybean           3C,8H      9H                                               Rice              10E        10E                                              Sorghum           9H         10H                                              Sugar beet        4C,8G      9G                                               Cotton            9G         9G                                               ______________________________________                                    

What is claimed is:
 1. A compound of the formula: ##STR59## wherein E isCH₂ or a single bond;W is O; R is H or CH₃ ; R₁ is F, Cl, Br, NO₂, C₁-C₄ alkyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy, OCH₂ CH₂ OCH₃, C₁ -C₄ haloalkoxy, C₃ -C₄alkenyloxy, C₂ -C₄ haloalkenyloxy, C₃ -C₄ alkynyloxy, CO₂ R₃, CONR₄ R₅,SO₄ NR₄ R₅, SO₂ (OCH₃)CH₃, S(O)_(n) R₆, OSO₂ R₇, C₁ -C₂ alkylsubstituted with C₁ -C₂ alkoxy, OH or C₁ -C₂ alkylthio, CH₂ CN, C₆ H₅,##STR60## R₂ is CH(R₁₆)CN, CH(R₁₇)SCN, ##STR61## R₃ is C₁ -C₄ alkyl, C₃-C₄ alkenyl, C₃ -C₄ alkynyl, ##STR62## CH₂ CH₂ Cl, CH₂ CH₂ F, or C₁ -C₂alkyl substituted with OCH₃ or SCH₃ ; R₄ is C₁ -C₃ alkyl; R₅ is H or C₁-C₃ alkyl; R₄ and R₅ may be taken together to form (CH₂)₃ or (CH₂)₄ ; R₆is C₁ -C₃ alkyl, CH₂ CH═CH₂ or CH₂ C.tbd.CH; R₇ is C₁ -C₃ alkyl orN(CH₃)₂ ; R₈ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, CH₂ CH₂Cl, CH₂ CH₂ F, C₁ -C₂ alkyl substituted with OCH₃ or SCH₃ or C₃ -C₆cycloalkyl; R₉ is C₁ -C₂ alkyl; R₁₀ and R₁₁ are independently C₁ -C₂alkyl, C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, NHCH₃ or N(CH₃)₂ ; R₁₂ and R₁₃are independently H or C₁ -C₂ alkyl; R₁₄ is C₁ -C₃ alkyl; R₁₅ is H orCH₃ ; R₁₆ is H, C₁ -C₂ alkyl or F; R₁₇ is H or C₁ -C₂ alkyl; R₁₈ is C₁-C₂ alkyl; R₁₉ is H, Si(CH₃)₃ or C₁ -C₂ alkyl; R₂₀ is H or C₁ -C₂ alkyl;p is 1 or 2; n is 0, 1, or 2; A is ##STR63## X₃ is CH₃ or OCH₃ ; andtheir agriculturally suitable salts; provided that (1) when R₂ isC(O)R₁₇, then R₁ is other than C₁ -C₄ haloalkyl or C₂ alkyl substitutedwith C₁ -C₂ alkoxy, OH or C₁ -C₂ alkylthio; and (2) when R₂ is C(O)R₁₇then R₁ is other than SO₂ NR₄ R₅ and SO₂ N(OCH₃)CH₃.
 2. A compound ofclaim 1 wherein R is H.
 3. A compound of claim 2 where E is a singlebond.
 4. A compound of claim 3 whereR₂ is CH₂ CN, CH₂ N₃, ##STR64##
 5. Acompound of claim 4 wherein R₁ is F, Cl, Br, NO₂, C₁ -C₃ alkyl, C₁ -C₂alkyl substituted with 1-3 F or Cl or 1 Br, C₂ -C₃ alkenyl, C₂ -C₃alkenyl substituted with 1-3 F or Cl, C₁ -C₂ alkoxy, C₁ -C₂ alkoxysubstituted with 1-3 F or Cl or 1-Br, allyloxy, propargyloxy,OC(Cl)═CHCl, CO₂ CH₃, CO₂ C₂ H₅, CO₂ CH₂ CH═CH₂, CO₂ CH₂ CH₂ Cl, CO₂ CH₂CH₂ OCH₃, CONH(C₁ -C₂ alkyl), CONCH₃ (C₁ -C₂ alkyl, SO₂ N(OCH₃)CH₃, SO₂NH(C₁ -C₂ alkyl), SO₂ N(C₁ -C₂ alkyl)₂, S(O)_(n) C₁ -C₃ alkyl, OSO₂ C₁-C₃ alkyl, C₁ -C₂ alkyl substituted with OCH₃ or SCH₃, C₆ H₅ and R₁ --A,R₁ --B, R₁ --C, R₁ --D, R₁ --E, R₁ --F, R₁ --G, R₁ --H, R₁ --I, R₁ --J,R₁ --K, R₁ --L, R₁ --M, R₁ --N, R₁ --O, R₁ --P, R₁ --Q R₁ --R, R₁ --S,R₁ --t, R₁ --U, R₁ --V or R₁ --W.
 6. A compound of claim 5 whereR₁ is F,Cl, Br, NO₂, CH₃, CF₃ C₁ -C₂ alkoxy, allyloxy, OC(Cl)═CHCl, CO₂ CH₃, CO₂C₂ H₅, CO₂ NHCH₃, CO₂ N(CH₃)₂, SO₂ NHCH₃ SO₂ N(CH₃)₂, SO₂ CH₃, SO₂ C₂H₅, OSO₂ CH₃, OSO₂ C₂ H₅, R₁ --A, R₁ --B or R₁ --C.
 7. A compositionsuitable for controlling the growth of undesired vegetation whichcomprises an effective amount of a compound of claim 1 and at least oneof the following: surfactant, solid or liquid diluent.
 8. A compositionsuitable for controlling the growth of undesired vegetation whichcomprises an effective amount of a compound of claim 2 and at least oneof the following: surfactant, solid or liquid diluent.
 9. A compositionsuitable for controlling the growth of undesired vegetation whichcomprises an effective amount of a compound of claim 3 and at least oneof the following: surfactant, solid or liquid diluent.
 10. A compositionsuitable for controlling the growth of undesired vegetation whichcomprises an effective amount of a compound of claim 4 and at least oneof the following: surfactant, solid or liquid diluent.
 11. A compositionsuitable for controlling the growth of undesired vegetation whichcomprises an effective amount of a compound of claim 5 and at least oneof the following: surfactant, solid or liquid diluent.
 12. A compositionsuitable for controlling the growth of undesired vegetation whichcomprises an effective amount of a compound of claim 6 and at least oneof the following: surfactant, solid or liquid diluent.
 13. A method ofcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound ofclaim
 1. 14. A method for controlling the growth of undesired vegetationwhich comprises applying to the locus to be protected an effectiveamount of a compound of claim
 2. 15. A method for controlling the growthof undesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 3. 16. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim4.
 17. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 5. 18. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim 6.